Methyl Ethyl Ketone → 2-Methyl-2-(1-pyrrolidinyl)butanenitrile

HRID 20802Notes

Reaction equation

HRID 20802 reaction equation
N1CCC[CH2:2]1.CC(=O)CC.[C-]#N.[K+].[CH3:14][C:15]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:18])[C:16]#[N:17]>O>[CH3:14][C:15]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH2:18][CH3:2])[C:16]#[N:17]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 9032Potassium CyanideHCID 31268PyrrolidineHCID 125706472-Methyl-2-(pyrrolidin-1-yl)propanenitrile

Product 1

HCID 438028382-Methyl-2-(1-pyrrolidinyl)butanenitrileYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (9.6 g, 63%) was prepared from pyrrolidine (8.35 ml, 0.1 mol), 2-butanone (8.96 g, 0.1 mol) and potassium cyanide (6.51 g, 0.1 mol) in water (50 ml) in a similar manner to that described in D4. 1H NMR (CDCl3) δ: 1.06 (3H, t, J=7.2 Hz), 1.45 (3H, s), 1.66-1.93 (6H, m), 2.70-2.75 (4H, m).

Sources & evidence

ORD record
ord-fdeac761ed134756b5116e11b959d866
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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