Dimethylformamide → 2-cyclohexylacetonitrile

HRID 1107434Notes

Reaction equation

HRID 1107434 reaction equation
[C-:1]#N.[Na+].[CH:4]1(Br)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C[N:12]([CH:14]=O)C>>[CH:4]1([CH2:1][C:14]#[N:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7960Cyclohexyl bromideHCID 8929Sodium Cyanide

Product 1

HCID 109534882-cyclohexylacetonitrile

Procedure

A solution of sodium cyanide (2.77 g, 56.5 mmol) in 70 ml of DMF was treated with cyclohexyl bromide (7.9 ml, 56.5 mmol), under N2. The reaction mixture was reacted for 48 hours and then partitioned between EtOAc and H2O. The resultant layers were separated and the organic layer was concentrated in vacuo. The crude material was purified using flash chromatography (eluent of 5% EtOAc in hexanes).

Workup

  1. customThe reaction mixture was reacted for 48 hours
  2. custompartitioned between EtOAc and H2O
  3. customThe resultant layers were separated
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe crude material was purified

Sources & evidence

ORD record
ord-bb38abc9a42b42f4952d8a23d5ebc271
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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