Cyclohexylamine → 2-Cyano-N-cyclohexylacetamide

HRID 1160527Notes

Reaction equation

HRID 1160527 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[CH:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:1]([CH2:3][C:4]([NH:13][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 7061432-Cyano-N-cyclohexylacetamideYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanoacetic acid (4.26 g, 50 mmol) and cyclohexylamine (4.96 g, 50 mmol) were dissolved in DCM (100 mL). EDCI (10.51 g, 55 mmol) was added and the mixture stiffed at ambient temperature for 24 h. The reaction mixture was washed with water (2×100 mL), dried (MgSO4) and evaporated to leave a yellow solid residue which was purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-100%) to provide the title compound as a white solid (5.66 g, 68%).

Workup

  1. washThe reaction mixture was washed with water (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a yellow solid residue which
  5. customwas purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-100%)

Sources & evidence

ORD record
ord-37d137154a28438bbb801fd5ed2f7475
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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