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

HRID 354108Notes

Reaction equation

HRID 354108 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-fa762bcea0dd4df597f0405e7ef44b23
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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