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【结 构 式】

【分子编号】51931

【品名】butyl 2-(4-amino-1-piperidinyl)acetate

【CA登记号】

【 分 子 式 】C11H22N2O2

【 分 子 量 】214.30796

【元素组成】C 61.65% H 10.35% N 13.07% O 14.93%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The condensation of 4-(tert-butoxycarbonylamino)piperidine (I) with butyl chloroacetate (II) by means of TEA in hot DMF gives butyl 2-[4-(tert-butoxycarbonylamino)piperdin-1-yl]acetate (III), which is deprotected with HCl in isopropanol to yield butyl 2-(4-aminopiperidin-1-yl)acetate (IV). Finally, this compound is condensed with 4-amino-5-chloro-2-methoxybenzoic acid (V) by means of ethyl chloroacetate, TEA and K2CO3 in THF to afford the target benzamide.

1 Sakaguchi, J.; Kato, H.; Kado, N. (Hokuriku Seiyaku Co., Ltd.); Benzamide derivs. and drugs containing the same. EP 1149832; JP 2000290254; WO 0046201 .
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) 41601 tert-butyl 4-piperidinylcarbamate; 4-tert-Boc-aminopiperidine 73874-95-0 C10H20N2O2 详情 详情
(II) 14595 n-Butyl Chloroacetate; butyl 2-chloroacetate 590-02-3 C6H11ClO2 详情 详情
(III) 51930 butyl 2-[4-[(tert-butoxycarbonyl)amino]-1-piperidinyl]acetate C16H30N2O4 详情 详情
(IV) 51931 butyl 2-(4-amino-1-piperidinyl)acetate C11H22N2O2 详情 详情
(V) 12419 4-Amino-5-chloro-2-methoxybenzoic acid 7206-70-4 C8H8ClNO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

A new synthetic route has been reported. 4-Amino-1-benzylpiperidine (I) was protected as the t-butyl carbamate (II) using Boc2O, and the N-benzyl group was subsequently removed by transfer hydrogenolysis, yielding 4-(t-butoxycarbonylamino)piperidine (III). Butyl chloroacetate (V), prepared by treatment of chloroacetyl chloride (IV) with n-butanol, was then condensed with piperidine (III) to afford (VI). After acidic cleavage of the Boc protecting group of (VI), the resultant amino piperidine (VII) was acylated with the mixed anhydride (VIII) to provide the target amide.

1 Sakaguchi, J.; et al.; An improved synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224). Chem Pharm Bull 2001, 49, 6, 788.
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) 34808 1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine 50541-93-0 C12H18N2 详情 详情
(II) 56563 tert-butyl 1-benzyl-4-piperidinylcarbamate C17H26N2O2 详情 详情
(III) 41601 tert-butyl 4-piperidinylcarbamate; 4-tert-Boc-aminopiperidine 73874-95-0 C10H20N2O2 详情 详情
(IV) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(V) 14595 n-Butyl Chloroacetate; butyl 2-chloroacetate 590-02-3 C6H11ClO2 详情 详情
(VI) 51930 butyl 2-[4-[(tert-butoxycarbonyl)amino]-1-piperidinyl]acetate C16H30N2O4 详情 详情
(VII) 51931 butyl 2-(4-amino-1-piperidinyl)acetate C11H22N2O2 详情 详情
(VIII) 29299 4-Amino-5-chloro-2-methoxybenzoic acid methoxycarbonyl anhydride C10H10ClNO5 详情 详情
Extended Information