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

HRID 2414861Notes

Reaction equation

HRID 2414861 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-70ad2a6870bb443787e6550d8cc68c66
Source dataset
uspto-grants-2004_11
Patent number
US06815458B2

Reaction notes

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