GB1411666A - Tetrahydro-1,4-oxazines and process for preparing the same - Google Patents
Tetrahydro-1,4-oxazines and process for preparing the sameInfo
- Publication number
- GB1411666A GB1411666A GB1771873A GB1771873A GB1411666A GB 1411666 A GB1411666 A GB 1411666A GB 1771873 A GB1771873 A GB 1771873A GB 1771873 A GB1771873 A GB 1771873A GB 1411666 A GB1411666 A GB 1411666A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- methylol
- aralkyl
- hydrogen
- group
- 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
- 150000002780 morpholines Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cinnamyl ester C Chemical compound 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000003974 aralkylamines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
1411666 Tetrahydro-1,4-oxazines CENTRE EUROPEEN DE RECHERCHES MAUVER NAY 12 April 1973 [13 April l972 17718/73 Heading C2C The invention comprises compounds of general formula when R 1 is a methylol, carboxylic acid or carboxylic ester group and R 2 is hydrogen alkyl or aralkyl, and salts thereof with acids. Compounds in which R 1 is carboxylic ester and R 2 is alkyl or aralkyl are prepared by treating a cinnamyl ester C 6 H 5 CH = CHR 1 with a tertiary alkyl hypobromite (e.g. tertiary butyl) in the presence of an excess of ethylene chlorohydrin, and treating the resultant chloroethoxybrominated product with a primary alkyl or aralkyl amine R 2 NH 2 . The ester group may then be saponified to give the acid or reduced with a metal hydride (e.g. lithium aluminium hydride) to the methylol group, and the alkyl or aralkyl group R 2 may be replaced by hydrogen by catalytic hydrogenation, e.g. with palladium as catalyst. In examples R 1 is carboxy, carboxymethyl, carboxyethyl and methylol and R 2 is hydrogen, p-butyl and benzyl. Hydrochloride addition salts of the products are prepared, and also a derivative in which R 1 is methylol and R 2 is acetyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7212892A FR2179578B1 (en) | 1972-04-13 | 1972-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1411666A true GB1411666A (en) | 1975-10-29 |
Family
ID=9096778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1771873A Expired GB1411666A (en) | 1972-04-13 | 1973-04-12 | Tetrahydro-1,4-oxazines and process for preparing the same |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2318024A1 (en) |
| FR (1) | FR2179578B1 (en) |
| GB (1) | GB1411666A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013526583A (en) * | 2010-05-21 | 2013-06-24 | リサーチ・トライアングル・インスティチュート | Phenylmorpholine and its analogs |
| CN114213354A (en) * | 2021-12-30 | 2022-03-22 | 上海皓元生物医药科技有限公司 | Preparation method of trans-2- (substituted phenyl) -3-hydroxymethyl morpholine |
-
1972
- 1972-04-13 FR FR7212892A patent/FR2179578B1/fr not_active Expired
-
1973
- 1973-04-10 DE DE19732318024 patent/DE2318024A1/en active Pending
- 1973-04-12 GB GB1771873A patent/GB1411666A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013526583A (en) * | 2010-05-21 | 2013-06-24 | リサーチ・トライアングル・インスティチュート | Phenylmorpholine and its analogs |
| AU2011255276B2 (en) * | 2010-05-21 | 2016-09-22 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| US9617229B2 (en) | 2010-05-21 | 2017-04-11 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| CN114213354A (en) * | 2021-12-30 | 2022-03-22 | 上海皓元生物医药科技有限公司 | Preparation method of trans-2- (substituted phenyl) -3-hydroxymethyl morpholine |
| CN114213354B (en) * | 2021-12-30 | 2023-04-25 | 上海皓元生物医药科技有限公司 | Preparation method of trans-2- (substituted phenyl) -3-oxymorphone |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2318024A1 (en) | 1973-10-31 |
| FR2179578A1 (en) | 1973-11-23 |
| FR2179578B1 (en) | 1976-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1433817A (en) | N-heteroarylmethyl-benzomorphane derivatives | |
| GB1300526A (en) | Process for the preparation of hydroxy-fatty acid esters | |
| GB835526A (en) | A method for preparing polyene-carboxylic acids and their derivatives | |
| ES273999A1 (en) | Process for the preparation of new -carboline-carboxylic acid amide derivatives | |
| GB925429A (en) | Indole derivatives | |
| GB1440767A (en) | Oxidation process for the manufacture of 4-aminodiphenylamine and related higher amines | |
| GB1411666A (en) | Tetrahydro-1,4-oxazines and process for preparing the same | |
| ES405276A1 (en) | Pyrimidinylphrazolone derivative and process of preparing the same | |
| GB1317499A (en) | Process for the manufacture of n,n-dihaloalkyl-2,6-dinitro-4- substituted anilines | |
| GB1003659A (en) | Novel phenylalkanolamine derivatives and a method for their production | |
| ES429959A1 (en) | Procedure for the preparation of new analogosous compounds of prostanic acids, not present in nature (Machine-translation by Google Translate, not legally binding) | |
| GB586645A (en) | Improvements relating to the synthesis of amino acid derivatives and salts thereof | |
| DE3061787D1 (en) | Process for preparing derivatives of 6-amino-6-desoxy-2,3-0-isopropylidene-alpha-l-sorbofuranose and intermediates of the process | |
| GB501135A (en) | Manufacture of piperidine compounds | |
| GB1396615A (en) | Condensation process | |
| SE7503657L (en) | ||
| GB1190646A (en) | Aryl-Substituted Aliphatic Secondary Amines | |
| US3239563A (en) | Reduction of 1-phenyl-nitropropane-1, 3-diol | |
| GB1245997A (en) | Improvements in the production of amines | |
| GB1032872A (en) | Aryloxy acetic acid amides and processes for their production | |
| GB1443310A (en) | Process for the production of neohesperidine dihydrochalcone | |
| Morrison et al. | 302. Synthetic analgesics. Part V. Compounds related to pethidine | |
| ES414765A1 (en) | Procedure for obtaining a new adamantamine derivative. (Machine-translation by Google Translate, not legally binding) | |
| GB960182A (en) | New isoquinoline derivatives and their preparation | |
| GB966682A (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |