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【结 构 式】

【分子编号】37463

【品名】4-(4-chlorophenyl)-N-heptylbutanamide

【CA登记号】

【 分 子 式 】C17H26ClNO

【 分 子 量 】295.85228

【元素组成】C 69.02% H 8.86% Cl 11.98% N 4.73% O 5.41%

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:(V)

The reaction of p-chlorobenzaldehyde (I) sodium cyanide and ethyl acetate gives ethyl 4-(p-chlorophenyl)-4-oxobutyrate (II), which is hydrolyzed with KOH to the corresponding free acid (III). The reduction of (III) with Zn and aqueous HCl affords 4-(p-chlorophenyl)butyric acid (IV), which is condensed with heptylamine (B) by means of oxalyl chloride (A) in refluxing benzene to yield N-heptyl-4-(p-chlorophenyl)butyramide (V), which is reduced with diborane in refluxing THF to afford N-heptyl-4-(p-chlorophenyl)butylamine (VI). The acetylation of (VI) with acetyl chloride (C) by means of Na2CO3 in acetone gives N-acetyl-N-heptyl-4-(p-chlorophenyl)butylamine (VII), which is reduced with diborane as before to yield N-ethyl-N-heptyl-4-(p-chlorophenyl)butylamine (VIII). The quaternization of (VIII) with refluxing ethyl bromide (D) gives N,N-diethyl-N-heptyl-4-(p-chlorophenyl)butylammonium bromide (IX), which by elution through a column with Dowex 1-X8, hydroxide form, resin is converted into N,N-diethyl-N-heptyl-4-(p-chlorophenyl)butyl ammonium hydroxide (X). Finally, this compound is salified with diluted aqueous phosphoric acid.

1 Molloy, B.B.; Steinberg, M.I.; EP 0002604 .
2 Hillier, K.; Castaner, J.; Clofilium Phosphate. Drugs Fut 1981, 6, 12, 764.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 23252 1-heptanamine; heptylamine 111-68-2 C7H17N 详情 详情
(A) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(D) 30344 1-bromoethane;ethyl bromide 74-96-4 C2H5Br 详情 详情
(I) 29029 4-chlorobenzaldehyde 104-88-1 C7H5ClO 详情 详情
(II) 37460 ethyl 4-(4-chlorophenyl)-4-oxobutanoate C12H13ClO3 详情 详情
(III) 37461 4-(4-chlorophenyl)-4-oxobutyric acid 3984-34-7 C10H9ClO3 详情 详情
(IV) 37462 4-(4-chlorophenyl)butyric acid C10H11ClO2 详情 详情
(V) 37463 4-(4-chlorophenyl)-N-heptylbutanamide C17H26ClNO 详情 详情
(VI) 37464 N-[4-(4-chlorophenyl)butyl]-1-heptanamine; N-[4-(4-chlorophenyl)butyl]-N-heptylamine C17H28ClN 详情 详情
(VII) 37465 N-[4-(4-chlorophenyl)butyl]-N-heptylacetamide C19H30ClNO 详情 详情
(VIII) 37466 N-[4-(4-chlorophenyl)butyl]-N-ethyl-N-heptylamine; N-[4-(4-chlorophenyl)butyl]-N-ethyl-1-heptanamine C19H32ClN 详情 详情
(IX) 37467 N-[4-(4-chlorophenyl)butyl]-N,N-diethyl-1-heptanaminium bromide C21H37BrClN 详情 详情
(X) 37468 N-[4-(4-chlorophenyl)butyl]-N,N-diethyl-1-heptanaminium hydroxide C21H38ClNO 详情 详情
(C) 19273 acetyl chloride 75-36-5 C2H3ClO 详情 详情
Extended Information