Crotononitrile → 4-(4-Fluorophenyl)-β-methyl-1-piperidinepropanenitrile

HRID 429057Notes

Reaction equation

HRID 429057 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14](#[N:18])/[CH:15]=[CH:16]/[CH3:17]>CO>[C:14]([CH2:15][CH:16]([N:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1)[CH3:17])#[N:18]

Participants

4

Reactant 2

HCID 637921CrotononitrileHCID 27591364-(4-Fluorophenyl)piperidine

Product 1

HCID 911828684-(4-Fluorophenyl)-β-methyl-1-piperidinepropanenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(4-fluorophenyl)piperidine (360 mg, 2 mmol) and crotononitrile (0.33 mL, 4 mmol) in methanol (4 mL) was refluxed for five hours. The solvent was concentrated under vacuum and the residue triturated with hexane/diethyl ether to give the racemic title compound as a solid.

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. customthe residue triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-cb57cbf5692a4e1398d8d1901628f803
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Reaction notes

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