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

HRID 1082133Notes

Reaction equation

HRID 1082133 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-254ea29eb8be400f94a87657c6f1d3e6
Source dataset
uspto-grants-1996_12
Patent number
US05589497

Reaction notes

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