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Cyclopentanone → 1-(Diethylamino)cyclopentanecarbonitrile

HRID 20792
Notes
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Reaction equation

HRID 20792 reaction equation
Cl.[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].[C:7]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[C-]#N.[K+].[CH3:16][N:17](C)C1(C#N)CCCC1>O>[CH2:2]([N:4]([CH2:5][CH3:6])[C:7]1([C:16]#[N:17])[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:3]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 10197650Diethylammonium chlorideHCID 107730491-(Dimethylamino)cyclopentanecarbonitrile

Product 1

HCID 242767611-(Diethylamino)cyclopentanecarbonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (2.06 g, 62%) was prepared from diethylamine hydrochloride (2.14 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 D1. 1H NMR (CDCl3) δ: 1.11 (6H, t, J=7 Hz), 1.78-1.88 (6H, m), 2.22 (2H, m), 2.71 (4H, q, J=7 Hz).

Sources & evidence

ORD record
ord-10ca5a0bc6414f21970b59dd43514c14
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745642B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes