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【结 构 式】

【药物名称】

【化学名称】N-(3,4-Dichlorophenyl)-2-(3,5-dimethylphenoxy)-N-(4-piperidinyl)acetamide

【CA登记号】

【 分 子 式 】C21H24Cl2N2O2

【 分 子 量 】407.34363

【开发单位】UCB Pharma (Originator)

【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT Reuptake Inhibitors, Tachykinin NK1 Antagonists

合成路线1

The reductocondensation of N-Boc-piperidin-4-one (I) with 3,4-dichloroaniline (II) by means of NaHB(OAc)3 in dichloroethane gives the secondary amine (III), which is acylated with chloroacetyl chloride (IV) by means of K2CO3 in dichloromethane to yield the chloroacetamide (V). The reaction of (V) with 3,5-dimethylphenol (VI) by means of Cs2CO3 in acetonitrile affords the aryl ether (VII), which is finally Boc deprotected with TFA in dichloromethane to provide the title trisubstituted acetamide.

1 Pirlot, N.; Balançon, L.; Berton, O.; Genicot, C.; Lamberty, Y.; Quéré, L.; Pasau, P.; Lallemand, B.; Talaga, P.; Ryckmans, T.; First dual NK1 antagonists-serotonin reuptake inhibitors: Synthesis and SAR of a new class of potential antidepressants. Bioorg Med Chem Lett 2002, 12, 2, 261.
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) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(II) 23629 3,4-dichloroaniline 95-76-1 C6H5Cl2N 详情 详情
(III) 54455 tert-butyl 4-(3,4-dichloroanilino)-1-piperidinecarboxylate C16H22Cl2N2O2 详情 详情
(IV) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(V) 54456 tert-butyl 4-[3,4-dichloro(2-chloroacetyl)anilino]-1-piperidinecarboxylate C18H23Cl3N2O3 详情 详情
(VI) 46786 3,5-dimethylphenol 108-68-9 C8H10O 详情 详情
(VII) 54457 tert-butyl 4-{3,4-dichloro[2-(3,5-dimethylphenoxy)acetyl]anilino}-1-piperidinecarboxylate C26H32Cl2N2O4 详情 详情
Extended Information