N-(1-Benzyl-4-phenyl-4-piperidinyl)-N-(2-fluorophenyl)propanamide -Drug Synthesis Database

【结构式】

【分子编号】13867

【品名】N-(1-Benzyl-4-phenyl-4-piperidinyl)-N-(2-fluorophenyl)propanamide

【CA登记号】

【分子式】C₂₇H₂₉FN₂O

【分子量】416.5385432

【元素组成】C 77.86% H 7.02% F 4.56% N 6.73% O 3.84%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

Condensation of 1-benzyl-4-piperidone (I) with 2-fluoroaniline (II) affords imine (III). Addition of phenyllithium (IV) to imine (III) gives amine (V), which is acylated with propionyl chloride and the resultant amide (VI) is debenzylated via 1-chloroethyl chloroformate in refluxing 1,2-dichloroethane followed by methanolysis to give (VII). Amine (VII)) is alkylated with 1-(2-bromoethyl)-4-ethyl-4,5-dihydro-1H-tetrazol-5-one(VIII) to yield A-3665. A-3665 hydrochloride is precipitated with dry HCl gas in ethyl ether.

参考文献中间体

合成目标

【1】 Kudzma, L.V.; Spencer, H.K.; Severnak, S.A. (BOC Health Care, Inc.); 4-Phenyl-4-[N-(phenyl)amido]piperidine derivs. and methods employing such cpds. AU 8824558; EP 0315405; JP 1990015061; JP 1990152963; US 4791121; US 4921864 .
【2】 Kudzma, L.V.; Ossipov, M.H.; Benvenga, M.J.; Spaulding, T.C.; Rudo, F.G.; A-3665. Drugs Fut 1990, 15, 6, 559.

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)	15750	(6R,7R)-3-[(acetoacetoxy)methyl]-7-[[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₇H₁₈N₆O₈S₂	详情	详情
(II)	22296	2-fluorophenylamine; 2-fluoroaniline	348-54-9	C₆H₆FN	详情	详情
(III)	13865	N-(1-Benzyl-4-piperidinylidene)-N-(2-fluorophenyl)amine; N-(1-Benzyl-4-piperidinylidene)-2-fluoroaniline		C₁₈H₁₉FN₂	详情	详情
(IV)	24014	Phenyllithium	591-51-5	C₆H₅Li	详情	详情
(V)	13866	N-(1-Benzyl-4-phenyl-4-piperidinyl)-N-(2-fluorophenyl)amine; 1-Benzyl-N-(2-fluorophenyl)-4-phenyl-4-piperidinamine		C₂₄H₂₅FN₂	详情	详情
(VI)	13867	N-(1-Benzyl-4-phenyl-4-piperidinyl)-N-(2-fluorophenyl)propanamide		C₂₇H₂₉FN₂O	详情	详情
(VII)	13868	N-(2-Fluorophenyl)-N-(4-phenyl-4-piperidinyl)propanamide		C₂₀H₂₃FN₂O	详情	详情
(VIII)	14721	1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one		C₅H₉BrN₄O	详情	详情

Extended Information