1-Benzyl-4-methylamino-3,3-dimethylpiperidine → HCID 10125063, compound

HRID 1865240Notes

Reaction equation

HRID 1865240 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[C:10]([CH3:17])([CH3:16])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[OH-].[Pd+2]>[CH3:15][NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1([CH3:17])[CH3:16]

Participants

5

Reactant 1

HCID 222788881-Benzyl-4-methylamino-3,3-dimethylpiperidine

Product 1

HCID 10125063HCID 10125063, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 20% Pd(OH)2 on carbon (0.15 g) and 1-benzyl-4-methylamino-3,3-dimethylpiperidine (0.5 g, 2.1 mmol) in methanol (10 ml) was stirred in hydrogen atmosphere (1 atm.) at 60° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-methylamino-3,3-dimethyl-piperidine. Yield 0.3 g (99%), C8H18N2, m/z 143 (M+1), PMR (CDCl3): 0.88 (s, 6H), 1.24 (m, 2H), 1.8 (bs, 2H, D2O exchangeable), 1.8 (m, 1H), 2.1 (m, 1H), 2.4 (s, 3H), 2.6 (d, 2H), 2.86 (m, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol and filtrate
  3. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-1e97a5531d7e4802b0af3b9a2752c4e7
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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