Cyclohexylamine → 2-Cyano-N-cyclohexylacetamide

HRID 1799393Notes

Reaction equation

HRID 1799393 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 stirred 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-8b293f05e7db4a81a127135a4d32ef1e
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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