Triethylamine → N-(1-Cyanocyclopentyl)pentanamide

HRID 1979076Notes

Reaction equation

HRID 1979076 reaction equation
[NH2:1][C:2]1([C:7]#[N:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:16](Cl)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20]>ClCCl>[C:7]([C:2]1([NH:1][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3]1)#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 21068971-Aminocyclopentanecarbonitrile

Product 1

HCID 11790092N-(1-Cyanocyclopentyl)pentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
32.5 °C

Procedure

To 11.0 g (0.1 mol) of 1-amino-1-cyanocyclopentane dissolved in 100 ml of dichloromethane, 15 ml 10.9 g (0.1 mol) of triethylamine was added, then dropwise 13 ml, 13 g (0.1 mol) of valeroyl chloride, while keeping the temperature at 25-35° C. The reaction mixture was stirred at 30-35° C. for 2 hours, then it was washed with water. The phases were separated, the organic phase was evaporated to obtain the pure title compound as an oil. The compound was identified by elementary analysis, IR, NMR and GC-MS spectomety.

Workup

  1. customat 25-35° C
  2. washit was washed with water
  3. customThe phases were separated
  4. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-52bcac1df94849daa9de5f87f89f776c
Source dataset
uspto-grants-2001_05
Patent number
US06239286B1

Reaction notes

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