Acrylonitrile → HCID 22725185, compound

HRID 322154Notes

Reaction equation

HRID 322154 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-601fc62344584280a326e540ae6c661c
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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