GB1411666A - Tetrahydro-1,4-oxazines and process for preparing the same - Google Patents

Tetrahydro-1,4-oxazines and process for preparing the same

Info

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
Application number
GB1771873A
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.)
Centre Europeen de Recherches Mauvernay CERM
Original Assignee
Centre Europeen de Recherches Mauvernay CERM
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.)
Filing date
Publication date
Application filed by Centre Europeen de Recherches Mauvernay CERM filed Critical Centre Europeen de Recherches Mauvernay CERM
Publication of GB1411666A publication Critical patent/GB1411666A/en
Expired legal-status Critical Current

Links

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

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.
GB1771873A 1972-04-13 1973-04-12 Tetrahydro-1,4-oxazines and process for preparing the same Expired GB1411666A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (5)

* Cited by examiner, † Cited by third party
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
FR2179578B1 (en) 1976-08-13
FR2179578A1 (en) 1973-11-23

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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