HCID 22278836, compound → HCID 10171257, compound

HRID 746869Notes

Reaction equation

HRID 746869 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-cd13757f06fa4c07af2d3914cb5edf5b
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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