Acrylonitrile → HCID 22725185, compound

HRID 396635Notes

Reaction equation

HRID 396635 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-ad241c8883e54b7ab3f89fccb91dadbc
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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