Cyclopentanone → 1-(Methylamino)cyclopentane-1-carbonitrile

HRID 1647820Notes

Reaction equation

HRID 1647820 reaction equation
[C-:1]#[N:2].[K+].[C:4]1(=O)[CH2:8][CH2:7][CH2:6][CH2:5]1.Cl.[CH3:11][NH2:12]>O>[CH3:1][NH:2][C:4]1([C:11]#[N:12])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 6364545Methylamine hydrochloride

Product 1

HCID 129454451-(Methylamino)cyclopentane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 6.5 of potassium cyanide in 13 ml of water was added at 15°-20° C. to a solution of 8.5 g of cyclopentanone and 7 g of methylamine hydrochloride in 7.5 ml of water and returned to room temperature; the mixture was stirred for 18 hours and extracted with methylene chloride. The organic phase was washed with aqueous sodium chloride, dried, and evaporated to dryness, and the residue was distilled to obtain 4.1 g of the expected product with a boiling point of 60° C.±0.3° C. at 7 mm of Hg.

Workup

  1. customreturned to room temperature
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with aqueous sodium chloride
  4. customdried
  5. customevaporated to dryness
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-c2db1dd5f5244959affd29e809fddc1d
Source dataset
uspto-grants-1995_07
Patent number
US05434176

Reaction notes

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