GB765874A - Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby - Google Patents
Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced therebyInfo
- Publication number
- GB765874A GB765874A GB3551353A GB3551353A GB765874A GB 765874 A GB765874 A GB 765874A GB 3551353 A GB3551353 A GB 3551353A GB 3551353 A GB3551353 A GB 3551353A GB 765874 A GB765874 A GB 765874A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridyl
- acetyl
- phenyl
- chlorophenyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical class C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 title abstract 6
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 2
- -1 3 - picolyl Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- KVSNHUCXGNKEKD-NSCUHMNNSA-N (e)-1-(4-chlorophenyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1=CC=C(Cl)C=C1 KVSNHUCXGNKEKD-NSCUHMNNSA-N 0.000 abstract 1
- FUJZJBCWPIOHHN-QHHAFSJGSA-N (e)-1-phenylbut-2-en-1-one Chemical compound C\C=C\C(=O)C1=CC=CC=C1 FUJZJBCWPIOHHN-QHHAFSJGSA-N 0.000 abstract 1
- YZBVUXSXZOYCEE-UHFFFAOYSA-N 1-(2-methylphenyl)-3-piperidin-1-yl-1-pyridin-2-ylpropan-1-ol Chemical compound C1(=C(C=CC=C1)C(CCN1CCCCC1)(O)C1=NC=CC=C1)C YZBVUXSXZOYCEE-UHFFFAOYSA-N 0.000 abstract 1
- MPQUKWCVXVBXIV-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-pyridin-2-yl-3-pyrrolidin-1-ylbutan-1-ol Chemical compound ClC1=CC=C(C=C1)C(CC(C)N1CCCC1)(O)C1=NC=CC=C1 MPQUKWCVXVBXIV-UHFFFAOYSA-N 0.000 abstract 1
- QGPKYCJDRMNUTK-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-pyridin-2-yl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound ClC1=CC=C(C=C1)C(CCN1CCCC1)(O)C1=NC=CC=C1 QGPKYCJDRMNUTK-UHFFFAOYSA-N 0.000 abstract 1
- KJFUKVWOUAIILJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-phenyl-1-pyridin-2-yl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound ClC1=CC=C(C=C1)C(C(CN1CCCC1)C1=CC=CC=C1)(O)C1=NC=CC=C1 KJFUKVWOUAIILJ-UHFFFAOYSA-N 0.000 abstract 1
- HXKNLFRSCIHHAD-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-phenyl-3-pyrrolidin-1-ylpropan-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=1C=CC=CC=1)CN1CCCC1 HXKNLFRSCIHHAD-UHFFFAOYSA-N 0.000 abstract 1
- ISWKMHGGUWPNSW-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-pyrrolidin-1-ylbutan-1-one Chemical compound C1CCCN1C(C)CC(=O)C1=CC=C(Cl)C=C1 ISWKMHGGUWPNSW-UHFFFAOYSA-N 0.000 abstract 1
- ZNUTYFDFJWCVSK-UHFFFAOYSA-N 1-phenyl-1-pyridin-2-yl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C1(=CC=CC=C1)C(CCN1CCCC1)(O)C1=NC=CC=C1 ZNUTYFDFJWCVSK-UHFFFAOYSA-N 0.000 abstract 1
- OXYBKQMXAKDTAK-UHFFFAOYSA-N 1-phenyl-3-piperidin-1-yl-1-pyridin-2-ylbutan-1-ol Chemical compound C1(=CC=CC=C1)C(CC(C)N1CCCCC1)(O)C1=NC=CC=C1 OXYBKQMXAKDTAK-UHFFFAOYSA-N 0.000 abstract 1
- YMZQTHVOMGBOGY-UHFFFAOYSA-N 1-phenyl-3-piperidin-1-ylbutan-1-one Chemical compound N1(CCCCC1)C(CC(=O)C1=CC=CC=C1)C YMZQTHVOMGBOGY-UHFFFAOYSA-N 0.000 abstract 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical group CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 abstract 1
- FUOWYCPLLURMMH-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-pyridin-2-ylcyclohexan-1-ol Chemical compound CN(C)CC1CCCCC1(O)C1=CC=CC=N1 FUOWYCPLLURMMH-UHFFFAOYSA-N 0.000 abstract 1
- QDHLEFBSGUGHCL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]cyclohexan-1-one Chemical compound CN(C)CC1CCCCC1=O QDHLEFBSGUGHCL-UHFFFAOYSA-N 0.000 abstract 1
- NHBIZLXNHCJNDP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C=1N=CC=CC=1)=CCN1CCCC1 NHBIZLXNHCJNDP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- COXTWEDOVSQDGZ-UHFFFAOYSA-N 4-piperidin-1-yl-2-pyridin-2-ylbutan-2-ol Chemical compound N1=C(C=CC=C1)C(C)(CCN1CCCCC1)O COXTWEDOVSQDGZ-UHFFFAOYSA-N 0.000 abstract 1
- IVZNRMILQKMEAQ-UHFFFAOYSA-N 4-piperidin-1-ylbutanal Chemical compound O=CCCCN1CCCCC1 IVZNRMILQKMEAQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006683 Mannich reaction Methods 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 abstract 1
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical group CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A method of preparing compounds containing the pyrrocoline nucleus comprises reacting a 1-(2 - pyridyl) - 3 - tertiary aminopropan - 1 - ol or a 1 - (2 - pyridyl) 3 - tertiary aminoprop - 1 - ene with acetic anhydride and separating the resulting pyrrocoline from the reaction mixture. The process is applicable to the reaction with acetic anhydride of compounds of the formula: <FORM:0765874/IV(b)/1> and <FORM:0765874/IV(b)/2> respectively, in which R1 is a phenyl or 2-thienyl group (either of which may carry as substituents chloro, bromo, alkyl or alkoxy groups), a 2-pyridyl or an alkyl group; R2 is hydrogen or a methyl or phenyl group; or R1 and R2 form a fully reduced cyclic structure having 5, 6, or 7 carbon atoms; R3 is hydrogen, or when R4 is hydrogen, is a methyl or phenyl group; R4 is hydrogen or methyl, except that when R1 is 2-pyridyl, R4 is hydrogen; NR5R6 is a tertiary amino group in which R5 and R6 may either be alkyl groups or together form a cyclic structure; R7 is phenyl or thienyl, which may carry substituents as listed for R1, the product being a pyrrocoline of the general formula: <FORM:0765874/IV(b)/3> in which R8 is an acetyl group or, when R3 is methyl or phenyl, R8 is methyl or phenyl. Reference is also made to the use of propionic anhydride. In examples: (1) 1-p-chlorophenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol is boiled with acetic anhydride to give 3-acetyl-1-p - chlorophenylpyrrocoline; (2) 1 - p - chlorophenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinoprop - 1 -ene refluxed with acetic anhydride, acetic acid and sodium acetate gives the same product as in (1); (3) and (4) 3-acetyl-1-phenylpyrrocoline is prepared similarly from 1 - phenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol and 1 phenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinoprop - 1-ene respectively. In further examples there are similarly prepared (from starting materials which include the carbinols described below or the corresponding allylamines) (5) and (6) 3 - acetyl - 2 - methyl - 1 - phenylpyrrocoline; (7) and (8) 3 - acetyl - 1 - p - chlorophenyl - 2-methyl - pyrrocoline; (9) and (10) 3 - acetyl-1 : 2 - diphenylpyrrocoline (11) 3 - acetyl - 1 - p - chlorophenyl - 2 - phenylpyrrocoline; (12) and (13) 1 - phenyl - 3 - methylpyrrocoline; (14) 1 - p - chlorophenyl - 3 - methylpyrrocoline; (15) and (16) 1 : 3 - diphenylpyrrocoline; (17) 3 - acetyl - 1 - p - anisylpyrrocoline; (18) 3-acetyl - 1 - o - tolylpyrrocoline; (19) 3 - acetyl-8 - methyl - 1 - phenylpyrrocoline; (20) 3-acetyl - 8 - methyl - 1 - p - chlorophenylpyrrocoline; (21) 3 - acetyl - 1 - (5 - chlorothienyl-2) pyrrocoline; (22) 3 - acetyl - 1 - (2 - pyridyl) pyrrocoline; (23) 3 - acetyl - 1 - methylpyrrocoline; (24) 3 - acetyl - 1 - ter - butylpyrrocoline; (25) 6 - acetyl - cyclohexa (9) - pyrrocoline for which the starting material, 2-dimethylaminomethyl - 1 - (2 - pyridyl) - cyclohexan - 1 - ol is prepared by the reaction of 2 - dimethylaminomethylcyclohexan - 1 - one with pyridyllithium. New carbinols, prepared for use as starting materials by the method of Specification 689,234, are 1-phenyl-1-(2-pyridyl)-3-piperidinoisobutan - 1 - ol 1 - p - chlorophenyl - 1 - (2-pyridyl) - 3 - piperidinoisobutan - 1 - ol, 1 : 2-diphenyl - 1 - (2 - pyridyl) - 3 - piperidinopropan-1 - ol, 1 - p - chlorophenyl - 2 - phenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol, 1-phenyl - 1 - (2 - pyridyl) - 3 - piperidinobutan-1 - ol, 1 - p - chlorophenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinobutan - 1 - ol, 1 : 3 - diphenyl - 1 - (2-pyridyl) - 3 - piperidinopropan - 1 - ol 1 - phenyl - 1 - (3 - picolyl - 2) - 3 - pyrrolidinopropan- 1-ol, 1 - p - chlorophenyl - 1 - (3 - picolyl - 2) - 3-pyrrolidinopropan - 1 - ol, 1 - o - tolyl - 1 - (2-pyridyl) - 3 - piperidinopropan - 1 - ol, 2 - (2-pyridyl) - 4 - piperidinobutan - 2 - ol, 3 - (2-pyridyl) - 2 : 2 - dimethyl - 5 - piperidinopentan-3 - ol, and 1 : 1 - di - (2 - pyridyl) - 3 - dimethylaminopropan-1-ol. As intermediates for such carbinols are prepared 1-phenyl-3-piperidinobutan - 1 - one (by reacting piperidine with crotonophenone), 1 - p - chlorophenyl - 3 - pyrrolidinobutan - 1 - one (by reacting pyrrolidine with p - chlorocrotonophenone), 1 : 3 - diphenyl - 3 - piperidinopropan - 1 - one (by reacting benzalacetophenone with piperidine), and 1 - phenyl - 3 - piperidinoisobutan - 1 - one, 1-p - chlorophenyl - 3 - piperidinoisobutan - 1-one, 1 : 2 - diphenyl - 3 - piperidinopropan - 1-one, 1 - p - chlorophenyl - 2 - phenyl - 3 - pyrrolidinopropan - 1 - one, 4 - piperidinobutan - 1-one and 5 - piperidino - 2 : 2 - dimethylpentan-3-one (by the Mannich reaction). Specifications 701,445 and 719,276 also are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3551353A GB765874A (en) | 1953-12-21 | 1953-12-21 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3551353A GB765874A (en) | 1953-12-21 | 1953-12-21 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB765874A true GB765874A (en) | 1957-01-16 |
Family
ID=10378580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3551353A Expired GB765874A (en) | 1953-12-21 | 1953-12-21 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB765874A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
| DE10261091A1 (en) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Saturated and unsaturated heteroarylcycloalkylmethyl amines |
| WO2022065938A1 (en) * | 2020-09-28 | 2022-03-31 | 아주대학교산학협력단 | Compound for aggregation-induced emission, composition for cell imaging using same, and use as cell-imaging contrast agent |
-
1953
- 1953-12-21 GB GB3551353A patent/GB765874A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
| DE10261091A1 (en) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Saturated and unsaturated heteroarylcycloalkylmethyl amines |
| US7384961B2 (en) | 2002-12-20 | 2008-06-10 | Gruenenthal Gmbh | Saturated and unsaturated heteroarylcycloalkylmethyl amines as anti-depressants |
| WO2022065938A1 (en) * | 2020-09-28 | 2022-03-31 | 아주대학교산학협력단 | Compound for aggregation-induced emission, composition for cell imaging using same, and use as cell-imaging contrast agent |
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