Dimethylformamide → 1-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindole

反応式

[C:1](=[O:4])([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:9][CH2:8]1.O[CH:28]([C:30]1[CH:38]=[CH:37][C:33](CCBr)=[CH:32][CH:31]=1)[CH3:29].[CH3:39]N(C)C=O>>[OH:4][CH:1]([CH:29]([C:10]1([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1)[CH2:28][C:30]1[CH:38]=[CH:37][CH:33]=[CH:32][CH:31]=1)[CH3:39]

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 220379271-(Piperidin-4-yl)-6-acetamidomethylindole

HCID 220379344-(1-Hydroxyethyl)phenethyl bromide

生成物 1

HCID 220380321-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindole収率 45.3%

実験手順

Potassium carbonate (0.5 g) was added to a solution of 1-(piperidin-4-yl)-6-acetamidomethylindole (0.10 g) obtained in Example 386-1) and 4-(1-hydroxyethyl)phenethyl bromide (0.07 g) obtained in Production Example 19 in N,N-dimethylformamide (5 ml) and the resultant mixture was stirred at 70° C. for 6 hr. Then the reaction mixtures were concentrated under reduced pressure and the residue was partitioned between chloroform (40 ml) and water (15 ml). The chloroform layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol system) to give the title compound (0.07 g) as a pale yellow wax (yield: 45.3%).