Cyclopentanone → 1-(Dimethylamino)cyclopentanecarbonitrile

HRID 20784

Reaction equation

HRID 20784 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C:5]1(=O)[CH2:9][CH2:8][CH2:7][CH2:6]1.[C-:11]#[N:12].[K+]>O>[CH3:2][N:3]([CH3:4])[C:5]1([C:11]#[N:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 107730491-(Dimethylamino)cyclopentanecarbonitrileYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred, ice cooled mixture of dimethylamine hydrochloride (26.32.g; 0.323 mol) and cyclopentanone (27.15 g; 0.323 mol) was added dropwise a solution of potassium cyanide (21.02 g; 0.323 mol) in water (170 ml) over 10 min. The mixture was stirred at room temperature overnight. Then, the mixture was extracted into diethylether (2×200 ml) and the combined organics were washed with brine (200 ml), dried (Na2SO4), and evaporated in vacuo to afford the title product as a colourless liquid (43 g, 96.5%)

Workup

  1. temperatureTo a stirred, ice cooled
  2. extractionThen, the mixture was extracted into diethylether (2×200 ml)
  3. washthe combined organics were washed with brine (200 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-211d410f60fe4ce2b7102f504244e6b9
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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