Cyclopentanone → 1-(1-Pyrrolidinyl)cyclopentanecarbonitrile

HRID 20790

Reaction equation

HRID 20790 reaction equation
N1CC[CH2:3][CH2:2]1.C1(=O)CCCC1.[C-]#N.[K+].[CH3:15][C:16]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)([CH3:19])[C:17]#[N:18]>O>[N:20]1([C:16]2([C:17]#[N:18])[CH2:19][CH2:3][CH2:2][CH2:15]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 31268PyrrolidineHCID 125706472-Methyl-2-(pyrrolidin-1-yl)propanenitrile

Product 1

HCID 5863471-(1-Pyrrolidinyl)cyclopentanecarbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (2.50 g, 76%) was prepared from pyrrolidine (1.42 g, 20 mmol), cyclopentanone (1.68 g, 20 mmol) and potassium cyanide (1.30 g, 20 mmol) in water (10 ml) in a similar manner to that described in D4. 1H NMR (CDCl3) δ: 1.80-1.90 (10H, m), 2.15 (2H, m), 2.71 (4H, m).

Sources & evidence

ORD record
ord-234c1ac459684641914088447f710e5a
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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