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

HRID 1063298Notes

Reaction equation

HRID 1063298 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-cfc8fe95b27046e48ef067f58934f6a5
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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