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Alifedrine hydrochloride, D-13625

1-环己基-3-[[(1R,2S)-1-羟基-1-苯基丙烷-2-基]氨基]丙-1-酮盐酸盐 阿利非君 Chemical Name: 1-Cyclohexyl-3-[(1S,2R)-2-hydroxy-1-methyl-2-phenethylamino]propan-1-one hydrochloride; 1-Cyclohexyl-3-[[(alphaS,betaR)-beta-hydroxy-alpha-m,ethylphenethyl]amino]-1-propane
CAS No. 72913-80-5, 78756-61-3 (free base)
项目整合开发状态: Phase III
项目研究机构: Degussa (Originator)
合成路线:Mannich reaction of acetylcyclohexane (V),paraformaldehyde and 1-norephedrine (I) in the presence of hydrochloric acid yields alifedrine hydrochloride.Mannich reaction of 1-acetylcyclohexene (VI) with paraformaldehyde and (I) followed by catalytic hydrogenation of the resulting beta-aminoketone (III) also gives alifedrine hydrochloride.

合成路线:For [14C]-labelling of alifedrine,the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII),which reacts with (I) to give alifedrine hydrochloride.Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

合成路线:Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV),which is obtained by reaction of (I) with paraformaldehyde in aqueous solution.Finally,alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).
📌 参考资料/链接:
参考文献标题:Alifedrine
文献作者:B鋒re,M.; Thiemer,K.; Engel,J.; Breuel,H.P.; Stroman,F.; Kleemann,A.
参考来源:Drugs Fut 1984,9(10),727

📄 详细内容


合成路线:For [14C]-labelling of alifedrine,the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII),which reacts with (I) to give alifedrine hydrochloride.Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献标题:Syntheses of 14C-1-erythro-norephedrine and its N-substitution products 14C-oxyfedrine and 14C-D 13,625
文献作者:Klingler,K.G.; Engel,J.; Bickel,E.
参考来源:Arzneim-Forsch Drug Res 1983,33(9),1213


合成路线:For [14C]-labelling of alifedrine,the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII),which reacts with (I) to give alifedrine hydrochloride.Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献标题:Novel cycloaliphatic enamines
文献作者:Engel,J.; et al.
参考来源:DE 3213371


合成路线:Mannich reaction of acetylcyclohexane (V),paraformaldehyde and 1-norephedrine (I) in the presence of hydrochloric acid yields alifedrine hydrochloride.Mannich reaction of 1-acetylcyclohexene (VI) with paraformaldehyde and (I) followed by catalytic hydrogenation of the resulting beta-aminoketone (III) also gives alifedrine hydrochloride.

合成路线:For [14C]-labelling of alifedrine,the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII),which reacts with (I) to give alifedrine hydrochloride.Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献标题:Cycloaliphatic ketoamines
文献作者:Engel,J.; et al.
参考来源:DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159


合成路线:Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV),which is obtained by reaction of (I) with paraformaldehyde in aqueous solution.Finally,alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).

参考文献标题:
文献作者:Tr鰉er,H.G.; Sheldrick,W.S.; Engel,J.
参考来源:Chem Ztg 1982,106(Suppl.1),427


合成路线:Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV),which is obtained by reaction of (I) with paraformaldehyde in aqueous solution.Finally,alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).
参考文献标题:Cycloaliphatic ketoamines
文献作者:Engel,J.; et al.
参考来源:DE 3043350


产品链接: CAS No. 72913-80-5››

产品链接: CAS No.78756-61-3››