2-cyano-N-cyclohexyl-N-methylacetamide → 3-Amino-N-cyclohexyl-N-methyl-propionamide

HRID 2088761Notes

Reaction equation

HRID 2088761 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:7])=[O:5])#[N:2].[H][H]>[Ni].N.CO>[NH2:2][CH2:1][CH2:3][C:4]([N:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 247058332-cyano-N-cyclohexyl-N-methylacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 167934313-Amino-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 2-cyano-N-cyclohexyl-N-methyl-acetamide (3.96 g, 0.022 mol), a known compound, (which may be prepared as disclosed in Osdene, Thomas S. et al. Journal of Medicinal Chemistry (1967), 10(2), 165-7; Osdene, Thomas S.; Santilli, Arthur A. U.S. Pat. No. 3,138,595) and Raney nickel (3 g) in NH3/MeOH (300 mL) was hydrogenated at normal pressure. After 2 equivalents of hydrogen were consumed, the catalyst was removed by filtration. The filtrate was evaporated, and toluene was added to the residue and then evaporated to yield a residue.

Workup

  1. customa known compound, (which may be prepared
  2. customthe catalyst was removed by filtration
  3. customThe filtrate was evaporated
  4. additiontoluene was added to the residue
  5. customevaporated
  6. customto yield a residue

Sources & evidence

ORD record
ord-23768688fe3f450c8b7410603401484e
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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