Acrylonitrile → HCID 21100522, compound

HRID 1352461Notes

Reaction equation

HRID 1352461 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH:6]([CH3:8])[NH:5][CH:4]1[CH2:9][OH:10].[C:11](#[N:14])[CH:12]=[CH2:13]>C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>[CH3:2][CH:3]1[CH2:7][CH:6]([CH3:8])[N:5]([CH2:13][CH2:12][C:11]#[N:14])[CH:4]1[CH2:9][OH:10]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 21100523HCID 21100523, compound

Product 1

HCID 21100522HCID 21100522, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 11430Potassium CarbonateSolvent

Procedure

The entire amount of 3,5-dimethyl-2-hydroxymethylpyrrolidine hydrochloride was dissolved in aqueous potassium carbonate solution (50 mL) and chloroform (50 mL), and acrylonitrile (20 mL) was added. The mixture was heated under reflux for 2 hr. After the completion of the reaction, the organic layer was separated and dried over magnesium sulfate. The solvent was concentrated and the obtained residue was purified by silica gel column chromatography. The fraction eluted with chloroform:methanol=40:1 was concentrated to give 3-(3,5-dimethyl-2-hydroxymethylpyrrolidin-1-yl)propionitrile (2.3 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customAfter the completion of the reaction
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. customthe obtained residue was purified by silica gel column chromatography
  8. washThe fraction eluted with chloroform
  9. concentrationmethanol=40:1 was concentrated

Sources & evidence

ORD record
ord-3b9be5de76114c238602c2dc5ed91ff2
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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