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【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%

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:(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
Extended Information