【结 构 式】 |
【分子编号】30965 【品名】2-phenoxyacetonitrile 【CA登记号】3598-14-9 |
【 分 子 式 】C8H7NO 【 分 子 量 】133.14972 【元素组成】C 72.17% H 5.3% N 10.52% O 12.02% |
合成路线1
该中间体在本合成路线中的序号:(II)The cyclization of 3-hydroxy-1,2-phenylenediamine (I) with 2-phenoxyacetonitrile (II) by means of sodium methoxide in methanol gives the benzimidazole (III), which is acylated with 4-(3-bromopropyl)piperidine-1-carboxylic acid tert-butyl ester (IV) by means of NaH and KI in hot DMF yielding the N-alkylated benzimidazole (V). The alkylation of the hydroxy group of (V) with 1-(3-bromopropyl)piperidine (VI) by means of NaH and KI as before affords the dialkylated benzimidazole (VII), which is deprotected with TFA in dichloromethane affording the free piperidine (VIII). Finally, the piperidine group of (VIII) is alkylated with 2-(4-iodophenyl)ethyl bromide (IX) by means of NaHCO3 in hot DMF.
【1】 Cantrell, B.E.; Zarrinmayeh, H.; Zimmerman, D.M.; et al.; Structure-activity relationship of a series of diaminoalkyl substituted benzimidazole as neuropeptide Y Y1 receptor antagonists. Bioorg Med Chem Lett 1999, 9, 5, 647. |
【2】 Nunes, A.M.; Zarrinmayeh, H.; Ornstein, P.L.; et al.; Synthesis and evaluation of a series of novel 2-[(4-chlorophenoxy)methyl]benzimidazoles as selective neuropeptide Y Y1 receptor antagonists. J Med Chem 1998, 41, 15, 2709. |
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) | 30964 | 2,3-diaminophenol | C6H8N2O | 详情 | 详情 | |
(II) | 30965 | 2-phenoxyacetonitrile | 3598-14-9 | C8H7NO | 详情 | 详情 |
(III) | 30966 | 2-(phenoxymethyl)-1H-benzimidazol-4-ol | C14H12N2O2 | 详情 | 详情 | |
(IV) | 30967 | tert-butyl 4-(3-bromopropyl)-1-piperidinecarboxylate | C13H24BrNO2 | 详情 | 详情 | |
(V) | 30968 | tert-butyl 4-[3-[4-hydroxy-2-(phenoxymethyl)-1H-benzimidazol-1-yl]propyl]-1-piperidinecarboxylate | C27H35N3O4 | 详情 | 详情 | |
(VI) | 30969 | 1-(3-bromopropyl)piperidine | C8H16BrN | 详情 | 详情 | |
(VII) | 30970 | tert-butyl 4-(3-[2-(phenoxymethyl)-4-[3-(1-piperidinyl)propoxy]-1H-benzimidazol-1-yl]propyl)-1-piperidinecarboxylate | C35H50N4O4 | 详情 | 详情 | |
(VIII) | 30971 | 2-(phenoxymethyl)-1-[3-(4-piperidinyl)propyl]-1H-benzimidazol-4-yl 3-(1-piperidinyl)propyl ether; 2-(phenoxymethyl)-4-[3-(1-piperidinyl)propoxy]-1-[3-(4-piperidinyl)propyl]-1H-benzimidazole | C30H42N4O2 | 详情 | 详情 | |
(IX) | 30972 | 1-(2-bromoethyl)-4-iodobenzene | C8H8BrI | 详情 | 详情 | |
(X) | 24298 | 2-(4-iodophenyl)acetic acid | 1798-06-7 | C8H7IO2 | 详情 | 详情 |
(XI) | 30973 | 2-(4-iodophenyl)-1-ethanol | C8H9IO | 详情 | 详情 |