1-Benzyl-4-piperidone → N-[(4-Methylphenyl)methyl]-1-(phenylmethyl)-4-piperidinamine

HRID 929694Notes

Reaction equation

HRID 929694 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.[BH4-].[Na+]>CO>[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 660354-MethylbenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 12146686N-[(4-Methylphenyl)methyl]-1-(phenylmethyl)-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-4-piperidone (1.74 g, 9.2 mmol) and 4-methylbenzylamine (0.97 g, 8 mmol) in methanol (30 ml) was added sodium borohydride (525 mg) in small portions over 30 min. The reaction mixture was stirred at room temperature. After 16 h, the mixture was concentrated. Water (30 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The combined organic layers were dried (Na2SO4), filtered, and concentrated to give 4-((4-methylphenyl)methyl)amino-1-phenylmethylpiperidine. The crude product was used without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. additionWater (30 ml) was added
  3. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1688deb06e164e35a1ef9284ceb5a98d
Source dataset
uspto-grants-2016_03
Patent number
US09296694B2

Reaction notes

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