2-amino-1-phenyl-1-propanol -Drug Synthesis Database

【结构式】

【分子编号】34264

【品名】2-amino-1-phenyl-1-propanol

【CA登记号】

【分子式】C₉H₁₃NO

【分子量】151.20836

【元素组成】C 71.49% H 8.67% N 9.26% O 10.58%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【1】 Engel, J.; et al.; Cycloaliphatic ketoamines. DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159 .
【2】 Bahre, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.; Alifedrine. Drugs Fut 1984, 9, 10, 727.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	34264	2-amino-1-phenyl-1-propanol		C₉H₁₃NO	详情	详情
(II)	34261	1-(1-cyclohexen-1-yl)-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-1-propanone		C₁₈H₂₅NO₂	详情	详情
(III)	34262	4-methyl-3-[(4-methyl-5-phenyl-1,3-oxazolidin-3-yl)methyl]-5-phenyl-1,3-oxazolidine		C₂₁H₂₆N₂O₂	详情	详情
(V)	34263	1-cyclohexyl-1-ethanone	823-76-7	C₈H₁₄O	详情	详情
(VI)	34260	1-(1-cyclohexen-1-yl)-1-ethanone	932-66-1	C₈H₁₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【1】 Engel, J.; et al.; Novel cycloaliphatic enamines. DE 3213371 .
【2】 Engel, J.; et al.; Cycloaliphatic ketoamines. DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159 .
【3】 Klingler, K.G.; Engel, J.; Bickel, E.; Syntheses of 14C-1-erythro-norephedrine and its N-substitution products 14C-oxyfedrine and 14C-D 13,625. Arzneim-Forsch Drug Res 1983, 33, 9, 1213.
【4】 Bahre, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.; Alifedrine. Drugs Fut 1984, 9, 10, 727.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	34264	2-amino-1-phenyl-1-propanol		C₉H₁₃NO	详情	详情
(V)	34263	1-cyclohexyl-1-ethanone	823-76-7	C₈H₁₄O	详情	详情
(VII)	17220	cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride	2719-27-9	C₇H₁₁ClO	详情	详情
(VIII)	34265	3-chloro-1-cyclohexyl-1-propanone		C₉H₁₅ClO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

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).

参考文献中间体

合成目标

【1】 Engel, J.; et al.; Cycloaliphatic ketoamines. DE 3043350 .
【2】 Tromer, H.G.; Sheldrick, W.S.; Engel, J.; Chem Ztg 1982, 106, Suppl. 1, 427.
【3】 Bahre, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.; Alifedrine. Drugs Fut 1984, 9, 10, 727.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	34264	2-amino-1-phenyl-1-propanol		C₉H₁₃NO	详情	详情
(IV)	34266	(E)-1-cyclohexyl-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-2-propen-1-one		C₁₈H₂₅NO₂	详情	详情
(VII)	17220	cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride	2719-27-9	C₇H₁₁ClO	详情	详情
(IX)	34267	(E)-3-chloro-1-cyclohexyl-2-propen-1-one		C₉H₁₃ClO	详情	详情
(X)	34268	3-cyclohexyl-3-oxopropanal		C₉H₁₄O₂	详情	详情

Extended Information