Sodium Hydroxide → 3-{4-[1-(4-Fluoro-benzyl)-1H-indol-3-yl]-piperidine-1-carbonyl}-benzonitrile

HRID 42234Notes

Reaction equation

HRID 42234 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])=[O:17])[CH2:12][CH2:11]2)=[CH:2]1.[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51]Br)=[CH:49][CH:48]=1>C1COCC1>[F:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])=[O:17])[CH2:12][CH2:11]3)=[CH:2]2)=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 2723671Tetrabutylammonium HydroxideHCID 574716313-[4-(1H-Indol-3-yl)-piperidine-1-carbonyl]-benzonitrile

Product 1

HCID 574716033-{4-[1-(4-Fluoro-benzyl)-1H-indol-3-yl]-piperidine-1-carbonyl}-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customThe layers are separated
  2. customthe organic solvent is removed under the reduced pressure
  3. custompurified by a silica gel flash column

Sources & evidence

ORD record
ord-c91fbd736325417ba00f180335ca975c
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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