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

HRID 2071934Notes

Reaction equation

HRID 2071934 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-020871c1ffce4c74b5571446c4f27abe
Source dataset
uspto-grants-1977_09
Patent number
US04049647

Reaction notes

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