JPH0312054B2 - - Google Patents

Info

Publication number: JPH0312054B2
Authority: JP; Japan
Prior art keywords: aminopyrrolidine; reaction; present; ammonia; water
Prior art date: 1985-10-11
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

Application number

JP22604185A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62201864A (ja

Inventor

Takeshi Hojo

Yasushi Sakamoto

Masumi Tsutsumi

Tamotsu Yamada

Kazuhiko Nakazono

Kazuya Ishimori

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tokyo Chemical Industries Co Ltd

Original Assignee

Tokyo Kasei Kogyo Co Ltd

Priority date (The priority date 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 date listed.)

1985-10-11

Filing date

1985-10-11

Publication date

1991-02-19

1985-10-11 Application filed by Tokyo Kasei Kogyo Co Ltd filed Critical Tokyo Kasei Kogyo Co Ltd

1985-10-11 Priority to JP22604185A priority Critical patent/JPS62201864A/ja

1986-10-07 Priority to US06/916,936 priority patent/US4785119A/en

1986-10-08 Priority to EP86113972A priority patent/EP0218249B1/en

1986-10-08 Priority to DE8686113972T priority patent/DE3686387T2/de

1987-09-05 Publication of JPS62201864A publication Critical patent/JPS62201864A/ja

1991-02-19 Publication of JPH0312054B2 publication Critical patent/JPH0312054B2/ja

Status Granted legal-status Critical Current

Links

NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 14
235000013844 butane Nutrition 0.000 description 10
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
-1 3-aminopyrrolidine compound Chemical class 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
239000002994 raw material Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 6
239000001273 butane Substances 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
UKFHIKGQGFCINK-UHFFFAOYSA-N 1,2,4-tribromobutane Chemical compound BrCCC(Br)CBr UKFHIKGQGFCINK-UHFFFAOYSA-N 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
PIQHRAXKAGNHCM-UHFFFAOYSA-N 1,2,4-trichlorobutane Chemical compound ClCCC(Cl)CCl PIQHRAXKAGNHCM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000002243 precursor Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
DAZXKDNMZIGPQQ-UHFFFAOYSA-N 1,2-dibromo-4-chlorobutane Chemical compound ClCCC(Br)CBr DAZXKDNMZIGPQQ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
150000005058 1,8-naphthyridines Chemical class 0.000 description 1
HBVNLKQGRZPGRP-UHFFFAOYSA-N 1-benzylpyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1=CC=CC=C1 HBVNLKQGRZPGRP-UHFFFAOYSA-N 0.000 description 1
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
OHSSXJLLWCUPEV-UHFFFAOYSA-N 4,4-dichlorobutan-1-ol Chemical compound OCCCC(Cl)Cl OHSSXJLLWCUPEV-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
WKEVRZCQFQDCIR-UHFFFAOYSA-N 4-chlorobut-1-ene Chemical compound ClCCC=C WKEVRZCQFQDCIR-UHFFFAOYSA-N 0.000 description 1
ZMMAJVZOYAEFNK-UHFFFAOYSA-N 4-oxo-3h-1,8-naphthyridine-3-carboxylic acid Chemical class C1=CC=C2C(=O)C(C(=O)O)C=NC2=N1 ZMMAJVZOYAEFNK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
KTVYGDJRKCXTRA-UHFFFAOYSA-N hydron;pyrrolidin-1-amine;chloride Chemical compound Cl.NN1CCCC1 KTVYGDJRKCXTRA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
NJPNCMOUEXEGBL-UHFFFAOYSA-N pyrrolidin-1-ium-3-ylazanium;dichloride Chemical compound Cl.Cl.NC1CCNC1 NJPNCMOUEXEGBL-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1

Landscapes

Pyrrole Compounds (AREA)

JP22604185A 1985-10-11 1985-10-11 ３―アミノピロリジンの製造法 Granted JPS62201864A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP22604185A JPS62201864A (ja)	1985-10-11	1985-10-11	３―アミノピロリジンの製造法
US06/916,936 US4785119A (en)	1985-10-11	1986-10-07	3-aminopyrrolidine compound and process for preparation thereof
EP86113972A EP0218249B1 (en)	1985-10-11	1986-10-08	Process for the production of 3-aminopyrrolidines
DE8686113972T DE3686387T2 (de)	1985-10-11	1986-10-08	Verfahren zur herstellung von 3-aminopyrrolidine.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP22604185A JPS62201864A (ja)	1985-10-11	1985-10-11	３―アミノピロリジンの製造法

Publications (2)

Publication Number	Publication Date
JPS62201864A JPS62201864A (ja)	1987-09-05
JPH0312054B2 true JPH0312054B2 (is)	1991-02-19

Family

ID=16838850

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP22604185A Granted JPS62201864A (ja)	1985-10-11	1985-10-11	３―アミノピロリジンの製造法

Country Status (1)

Country	Link
JP (1)	JPS62201864A (is)

1985
- 1985-10-11 JP JP22604185A patent/JPS62201864A/ja active Granted

Also Published As

Publication number	Publication date
JPS62201864A (ja)	1987-09-05

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JPH0312055B2 (is)	1991-02-19
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Legal Events

Date	Code	Title	Description
2005-02-19	LAPS	Cancellation because of no payment of annual fees