Acrylonitrile → 4-(2'-Cyanoethoxy) 1,2,2,6,6-pentamethylpiperidine

HRID 434442Notes

Reaction equation

HRID 434442 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH3:5][N:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]([OH:14])[CH2:8][C:7]1([CH3:16])[CH3:15].[OH-].[K+]>C1C=CC=CC=1>[C:1]([CH2:2][CH2:3][O:14][CH:9]1[CH2:8][C:7]([CH3:15])([CH3:16])[N:6]([CH3:5])[C:11]([CH3:13])([CH3:12])[CH2:10]1)#[N:4]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-

Product 1

HCID 204923584-(2'-Cyanoethoxy) 1,2,2,6,6-pentamethylpiperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.65 parts of acrylonitrile was added dropwise with stirring to a solution of 8.55 parts of 1,2,2,6,6-pentamethylpiperidin-4-ol and 0.30 parts of 40% potassium hydroxide solution in 80 parts of benzene. Stirring was continued at room temperature for 16 hours after which time the solution was washed with water, dried and the benzene solvent removed by distillation under reduced pressure. Fractional distillation of the residue, under reduced pressure gave 1.70 parts of 4-(2'-cyanoethoxy)-1,2,2,6,6-pentamethylpiperidine having a boiling point of 105°-6° C. at 0.1 mm of Hg and the following elemental analysis by weight:

Workup

  1. washafter which time the solution was washed with water
  2. customdried
  3. customthe benzene solvent removed by distillation under reduced pressure
  4. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-314c2ff11d4143bda105ae4ec5cf6605
Source dataset
uspto-grants-1983_08
Patent number
USRE031342

Reaction notes

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