Acrylonitrile → HCID 22725185, compound

HRID 382707Notes

Reaction equation

HRID 382707 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1>CCO>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:15][N:16]([CH2:3][CH2:2][C:1]#[N:4])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 4993578HCID 4993578, compound

Product 1

HCID 22725185HCID 22725185, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acrylonitrile (1.03 mL, 15.7 mmol, 2.50 equiv) was added at 0° C. to a solution of 4-(4-methoxyphenyl)-4-phenylpiperidine (1.68 g, 6.28 mmol, 1.00 equiv) in EtOH (20 mL) and the resulting solution was stirred for 1.5 hours at room temperature. After removal of the solvent, the residue was purified by flash chromatography (SiO2, EtOAc-CHCl3 1:3) to give 1.41 g (70%) of colorless oil, which was characterized spectroscopically.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by flash chromatography (SiO2, EtOAc-CHCl3 1:3)

Sources & evidence

ORD record
ord-e12157c3b48b483bb8774937fe043fea
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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