반응 #70512

ord-c91fbd736325417ba00f180335ca975c

반응 방정식

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

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The layers are separated
  2. 2
    기타the organic solvent is removed under the reduced pressure
  3. 3
    기타purified by a silica gel flash column

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08536168B2uspto-grants-2013_09