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【结 构 式】 
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【分子编号】33567 【品名】ethyl 4-[4-chloro(2-phenylacetyl)anilino]-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C22H25ClN2O3 【 分 子 量 】400.90488 【元素组成】C 65.91% H 6.29% Cl 8.84% N 6.99% O 11.97% |
合成路线1
该中间体在本合成路线中的序号：(V)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 |