HCID 22278836, compound → HCID 10171257, compound

HRID 1865242Notes

Reaction equation

HRID 1865242 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH3:16])[C:10]([CH3:18])([CH3:17])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[OH-].[Pd+2]>[CH2:15]([NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1([CH3:17])[CH3:18])[CH3:16]

Participants

5

Reactant 1

HCID 22278836HCID 22278836, compound

Product 1

HCID 10171257HCID 10171257, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 20% Pd(OH)2 on carbon (0.4 g) and 1-benzyl-4-ethylamino-3,3-dimethylpiperidine (1.3 g, 5.3 mmol) in methanol (10 ml) was stirred in hydrogen atmosphere (1 atm.) at ambient temperature for 15 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-ethylamino-3,3-dimethylpiperidine. Yield 0.8 g (97%), C9H20N2, m/z 157 (M+1), PMR (CDCl3): 0.9 (s, 3H), 1.06 (s, 3H), 1.18-1.38 (m, 5H), 1.85 (bs, 2H, D2O exchangeable), 1.64-2.8 (m, 6H), 2.94 (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-f78f1d5f29634efa9293d52775b39183
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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