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【结 构 式】

【分子编号】13702

【品名】N-[4-(4-Piperidinylcarbonyl)phenyl]methanesulfonamide

【CA登记号】

【 分 子 式 】C13H18N2O3S

【 分 子 量 】282.3636

【元素组成】C 55.3% H 6.43% N 9.92% O 17% S 11.36%

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)

The mesylation of aniline (I) with methanesulfonyl chloride gives the sulfonamide (II), which is condensed with 1-acetylpiperidine-4-carbonyl chloride (III) by means of AlCl3 in dichloromethane to give N-[4-(1-acetylpiperidin-4-ylcarbonyl)phenyl]methanesulfonamide (IV). Deacetylation of (IV) with HCl in water yields the piperidine (V), which is finally condensed with 2-methyl-6-vinylpyridine by means of sodium acetate in methanol - water. The same procedure has been performed with [14C]-labeled aniline in order to obtain [14C]-labeled E-4031.

1 Oinuma, H.; Yamanaka, M.; Miyake, K.; Hoshiko, T.; Minami, N.; Shoji, T.; Daiku, Y.; Sawada, K.; Nomoto, K. (Eisai Co., Ltd.); Piperidine deriv., pharmaceutical compsn. containing the same and use. EP 0235752; US 4876262; US 4996215; US 5118689; US 5179095 .
2 Miyake, K.; Yamanaka, M.; Katoh, H.; Shino, M.; Hamano, S.; Nomoto, K.-I.; Oinuma, H.; Sawada, K.; 4'-[(4-Piperidyl)carbonyl]methanesulfonanilides as potent, selective, bioavailable class III antiarrhythmic agents. J Med Chem 1990, 33, 3, 903.
3 Shino, M.; Oinuma, H.; Hamano, S.; Miyake, K.; Yamanaka, M.; Synthesis of antiarrhythmic [phenyl-14C]4'-[(4-piperidyl)carbonyl]methanesulfonanilides. J Label Compd Radiopharm 1990, 28, 8, 921.
4 Castaner, J.; Prous, J.; E-4031. Drugs Fut 1992, 17, 6, 455.
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) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(II) 13699 N-Phenylmethanesulfonamide; N-Phenyl methanesulfonamide 1197-22-4 C7H9NO2S 详情 详情
(III) 13700 1-Acetyl-4-piperidinecarbonyl chloride C8H12ClNO2 详情 详情
(IV) 13701 N-[4-[(1-Acetyl-4-piperidinyl)carbonyl]phenyl]methanesulfonamide C15H20N2O4S 详情 详情
(V) 13702 N-[4-(4-Piperidinylcarbonyl)phenyl]methanesulfonamide C13H18N2O3S 详情 详情
(VI) 13703 2-Methyl-6-vinylpyridine 1122-70-9 C8H9N 详情 详情
Extended Information