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【结 构 式】

【分子编号】33566

【品名】ethyl 4-(4-chloroanilino)-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C14H19ClN2O2

【 分 子 量 】282.76984

【元素组成】C 59.47% H 6.77% Cl 12.54% N 9.91% O 11.32%

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:(IV)

The reaction of p-chloroaniline (I) with ethyl 4-oxopiperidine-1-carboxylate (II) by means of tosyl chloride in refluxing toluene gives ethyl 4-(p-chlorophenylimino)piperidine-1-carboxylate (III), which is reduced with NaBH4 in refluxing methanol to afford ethyl 4-(p-chloroanilino)piperidine-1-carboxylate (IV). The acylation of (IV) with phenylacetyl chloride (A) in refluxing benzene yields ethyl 4-[N-(p-chlorophenyl)-N-(phenylacetyl)amino]piperidine-1-carboxylate (V), which is decarboxylated with hot aqueous HBr giving N-(p-chlorophenyl)-N-(piperidin-4-yl)phenylacetamide hydrochloride (VI). Finally, this compound is alkylated with 2-bromopropane (B) and Na2CO3 in refluxing butanol.

1 Hermans, H.K.; Sanczuk, S.; N-aryl-N-(1-L-4-piperidinyl)-arylacetamides. BE 0846473; US 4151286; US 4157393; ZA 7605684 .
2 Castaner, J.; Weetman, D.F.; Lorcainide hydrochloride. Drugs Fut 1978, 3, 7, 518.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 25890 2-phenylacetyl chloride;Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride 103-80-0 C8H7ClO 详情 详情
(B) 32658 2-bromopropane 75-26-3 C3H7Br 详情 详情
(I) 12034 4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline 106-47-8 C6H6ClN 详情 详情
(II) 13486 Ethyl 4-oxo-1-piperidinecarboxylate; N-Carbethoxy-4-piperidone 29976-53-2 C8H13NO3 详情 详情
(III) 33565 ethyl 4-[(4-chlorophenyl)imino]-1-piperidinecarboxylate C14H17ClN2O2 详情 详情
(IV) 33566 ethyl 4-(4-chloroanilino)-1-piperidinecarboxylate C14H19ClN2O2 详情 详情
(V) 33567 ethyl 4-[4-chloro(2-phenylacetyl)anilino]-1-piperidinecarboxylate C22H25ClN2O3 详情 详情
(VI) 33568 N-(4-chlorophenyl)-2-phenyl-N-(4-piperidinyl)acetamide C19H21ClN2O 详情 详情
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