【结 构 式】 |
【分子编号】12373 【品名】4-(4-Fluorobenzyl)-2-morpholinecarbonitrile 【CA登记号】 |
【 分 子 式 】C12H13FN2O 【 分 子 量 】220.2465032 【元素组成】C 65.44% H 5.95% F 8.63% N 12.72% O 7.26% |
合成路线1
该中间体在本合成路线中的序号:(III)The synthesis of deuterated mosapride citrate has been reported: The cyclization of N-(4-fluorobenzyl)ethanolamine (I) with 2-chloroacrylonitrile (II) in ethyl ether gives 4-(4-fluorobenzyl)morpholine-2-carbonitrile (III), which is submitted to alcoholysis with ethanol and H2SO4, yielding the corresponding ethyl ester (IV). The reduction of (IV) with deuterated sodium borohydride (NaBD4) in THF affords the deuterated hydroxymethyl derivative (V), which is condensed with phthalimide (VI) by means of triphenylphosphine and dimethyl azodicarboxylate (AZDC) in THF to give the N-substituted phthalimide (VII). The cleavage of (VII) with hydrazine hydrate in refluxing ethanol yields the deuterated methylamine derivative (VIII), which is finally condensed with 4-amino-5-chloro-2-ethoxybenzoic acid (IX) by means of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (EDCD) in dichloromethane, and treated with citric acid in the usual way.
【1】 Kato, S.; Hirokawa, Y.; Synthesis of deuterated mosapride citrate. J Label Compd Radiopharm 1995, 36, 10, 927. |
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) | 12334 | 2-[(4-Fluorobenzyl)amino]-1-ethanol | C9H12FNO | 详情 | 详情 | |
(II) | 12372 | 2-Chloroacrylonitrile | 920-37-6 | C3H2ClN | 详情 | 详情 |
(III) | 12373 | 4-(4-Fluorobenzyl)-2-morpholinecarbonitrile | C12H13FN2O | 详情 | 详情 | |
(IV) | 12374 | ethyl 4-(4-fluorobenzyl)-2-morpholinecarboxylate | C14H18FNO3 | 详情 | 详情 | |
(V) | 12375 | [4-(4-Fluorobenzyl)-2-morpholinyl]methanol | C12H16FNO2 | 详情 | 详情 | |
(VI) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
(VII) | 12377 | 2-[[4-(4-Fluorobenzyl)-2-morpholinyl]methyl]-1H-isoindole-1,3(2H)-dione | C20H19FN2O3 | 详情 | 详情 | |
(VIII) | 12378 | [4-(4-Fluorobenzyl)-2-morpholinyl]methylamine; [4-(4-Fluorobenzyl)-2-morpholinyl]methanamine | C12H17FN2O | 详情 | 详情 | |
(IX) | 12333 | 4-Amino-5-chloro-2-ethoxybenzoic acid | C9H10ClNO3 | 详情 | 详情 |