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

HRID 1968768Notes

Reaction equation

HRID 1968768 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 Osderie, 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 9) 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-cdc24b5fdd0a425a93bbe842dadd955c
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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