Ethyl 1-cyanocyclohexane-1-carboxylate → Ethyl 1-(aminomethyl)cyclohexane-1-carboxylate

HRID 1922201Notes

Reaction equation

HRID 1922201 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>[Ni].C(O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 10997650Ethyl 1-cyanocyclohexane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21840381Ethyl 1-(aminomethyl)cyclohexane-1-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Excess Raney Nickel in an ethanol slurry was added to a solution of 1-cyano-cyclohexanecarboxylic acid ethyl ester in ethanol under a nitrogen atmosphere. The nitrogen atmosphere was replaced with excess hydrogen gas and the mixture was allowed to stir overnight. The reaction mixture was filtered through celite and the solvent was removed. The compound was clean enough to continue without purification. 80% yield. MH+=186.2.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed
  3. customto continue without purification

Sources & evidence

ORD record
ord-d021f23b5c264095b84c940ff9912522
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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