Acetone → 2-Methyl-2-(pyrrolidin-1-yl)propanenitrile

HRID 20786Notes

Reaction equation

HRID 20786 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][C:7]([CH3:9])=O.[C-:10]#[N:11].[K+]>O>[CH3:6][C:7]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:9])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 180AcetoneHCID 9032Potassium CyanideHCID 31268Pyrrolidine

Product 1

HCID 125706472-Methyl-2-(pyrrolidin-1-yl)propanenitrileYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred, ice-cooled mixture of pyrrolidine (8.35 ml; 0.1 mol) and acetone (7.34 ml; 0.1 mol) was added a solution of potassium cyanide (6.51 g; 0.1 mol) in water (50 ml) dropwise over 10 min. After stirring at room temperature overnight, the crude reaction mixture was extracted with diethyl ether (2×250 ml) and the combined extracts washed with saturated brine (150 ml), dried (MgSO4), and evaporated under reduced pressure to afford the title product as a pale green liquid (10.7 g; 78%) which was used without further purification. 1H NMR (CDCl3) δ: 1.51 (6H, s), 1.80-1.90 (4H, m), 2.70-2.80 (4H, m).

Workup

  1. temperatureTo a stirred, ice-cooled
  2. customthe crude reaction mixture
  3. extractionwas extracted with diethyl ether (2×250 ml)
  4. washthe combined extracts washed with saturated brine (150 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ce705ff6717949d1a82e475a0fc3ec5c
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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