反应 #70512

ord-c91fbd736325417ba00f180335ca975c

反应方程式

N#Cc1cccc(C(=O)N2CCC(c3c[nH]c4ccccc34)CC2)c1
3-[4-(1H-Indol-3-yl)-piperidine-1-carbonyl]-benzonitrile
[Na+].[OH-]
NaOH
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetrabutyl ammonium hydroxide
Fc1ccc(CBr)cc1
4-fluoro-benzyl bromide
N#Cc1cccc(C(=O)N2CCC(c3cn(Cc4ccc(F)cc4)c4ccccc34)CC2)c1
3-{4-[1-(4-Fluoro-benzyl)-1H-indol-3-yl]-piperidine-1-carbonyl}-benzonitrile

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The layers are separated
  2. 2
    其他the organic solvent is removed under the reduced pressure
  3. 3
    其他purified by a silica gel flash column

实验过程

3-[4-(1H-Indol-3-yl)-piperidine-1-carbonyl]-benzonitrile (0.08 g, 0.24 mmol) is dissolved in 2 ml THF, then 2 ml of 50% NaOH, 0.2 ml tetrabutyl ammonium hydroxide (1.0M in MeOH), 4-fluoro-benzyl bromide (0.055 g, 0.29 mmol) are added and the reaction mixture is stirred at RT for 1.5 hours. The layers are separated and the organic solvent is removed under the reduced pressure, purified by a silica gel flash column using heptane and ethyl acetate as the elutes.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08536168B2uspto-grants-2013_09