Ammonium formate → (4-Amino-3-methyl-cyclohexylmethyl)-phenyl-amine

HRID 1914663Notes

Reaction equation

HRID 1914663 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH:10]1[CH3:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH:10]1[CH3:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67185307HCID 67185307, compound

Product 1

HCID 67185375(4-Amino-3-methyl-cyclohexylmethyl)-phenyl-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(4-Benzylamino-3-methyl-cyclohexylmethyl)-phenyl-amine (160 mg, 0.52 mmol) and ammonium formate (164 mg, 2.60 mmol) in EtOH (5 mL) is treated with 10% Pd/C (30 mg) and heated at reflux for 2 hours. The Pd/C is removed by filtration and washed with MeOH. The filtrate is concentrated in vacuo to afford the title compound which is used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe Pd/C is removed by filtration
  4. washwashed with MeOH
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-4680f0def9b64cd982a3d20f255e5b33
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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