Ammonium formate → 4-(Aminomethyl)cyclohexan-1-ol

HRID 1586155Notes

Reaction equation

HRID 1586155 reaction equation
C([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:16][CH:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH2:8])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21217695N-benzyl-N-(4-hydroxycyclohexyl methyl)amine

Product 1

HCID 148675294-(Aminomethyl)cyclohexan-1-olYield 25.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of N-benzyl-N-(4-hydroxycyclohexyl methyl)amine (8.5 g, 0.039 mol) in methanol (300 ml) under N2 is added ammonium formate (9.8 g, 0.0155 mol), followed by 10% palladium on carbon (1.0 g). The reaction mixture is refluxed for 3 hours, cooled to room temperature and filtered. The filtrate is evaporated to dryness and the residue is dissolved in CH2Cl2, filtered and the filtrate is evaporated to afford 1.3 g of 4-hydroxycyclohexylmethylamine.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated to dryness
  4. dissolutionthe residue is dissolved in CH2Cl2
  5. filtrationfiltered
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-adeffe2bada949f4a5b110f476f33c04
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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