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【结 构 式】

【分子编号】63283

【品名】4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylic acid

【CA登记号】

【 分 子 式 】C16H15ClO3

【 分 子 量 】290.746

【元素组成】C 66.1% H 5.2% Cl 12.19% O 16.51%

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:(V)

Fischer esterification of 4'-hydroxybiphenyl-4-carboxylic acid (I) with H2SO4/MeOH provides ester (II). The phenolic hydroxyl group is then alkylated with 1-bromo-3-chloropropane (III) in the presence of K2CO3 to furnish the chloropropyl ether (IV). Saponification of methyl ester (IV) with LiOH leads to carboxylic acid (V), which is further activated as the corresponding acid chloride (VI) upon heating in SOCl2. Acid chloride (VI) is subsequently coupled with morpholine (VII) to yield amide (VIII). Finally, alkyl chloride (VIII) is displaced with (R,R)-2,5-dimethylpyrrolidine (IX) in the presence of K2CO3 and KI to furnish the title compound.

1 Faghih, R.; Bennani, Y.L. (Abbott Laboratories Inc.); Aminoalkoxybiphenyl carboxamides as histamine-3 receptor ligands and their therapeutic applications. US 6316475; WO 0240461 .
2 Faghih, R.; Bennani, Y.; Aminoalkoxybiphenylcarboxamides as histamine-3 receptor ligands and their therapeutic applications. US 2002111340 .
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) 63280 4'-hydroxy[1,1'-biphenyl]-4-carboxylic acid C13H10O3 详情 详情
(II) 63281 methyl 4'-hydroxy[1,1'-biphenyl]-4-carboxylate C14H12O3 详情 详情
(III) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(IV) 63282 methyl 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylate C17H17ClO3 详情 详情
(V) 63283 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylic acid C16H15ClO3 详情 详情
(VI) 63284 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carbonyl chloride C16H14Cl2O2 详情 详情
(VII) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(VIII) 63285 [4'-(3-chloropropoxy)[1,1'-biphenyl]-4-yl](4-morpholinyl)methanone C20H22ClNO3 详情 详情
(IX) 63286 (2R,5R)-2,5-dimethylpyrrolidine C6H13N 详情 详情
Extended Information