Cyclopentanone → 1-(1-Azetidinyl)cyclopentanecarbonitrile

HRID 20794

Reaction equation

HRID 20794 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.C1(=O)CCCC1.[C-]#N.[K+].CN(C)[C:17]1([C:22]#[N:23])[CH2:21][CH2:20][CH2:19][CH2:18]1>O>[N:2]1([C:17]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 107730491-(Dimethylamino)cyclopentanecarbonitrileHCID 12308726Azetidine hydrochloride

Product 1

HCID 593477791-(1-Azetidinyl)cyclopentanecarbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (1.29 g, 43%) was prepared from azetidine hydrochloride (1.85 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: 1.70-1.82 (6H, m), 1.86 (2H, m), 2.07 (2H, quin, J=7 Hz), 3.32 (4H, t, J=7 Hz).

Sources & evidence

ORD record
ord-c1121d5546834bab92e2bff97a8f4126
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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