N-Benzyl-N-methyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine → Methyl((2-(1-(pyridin-4-yl)piperidin-4-yl)ethyl))amine

HRID 1193338Notes

Reaction equation

HRID 1193338 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO>[CH3:1][NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 66799326N-Benzyl-N-methyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine

Product 1

HCID 59597773Methyl((2-(1-(pyridin-4-yl)piperidin-4-yl)ethyl))amineYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Benzyl-N-methyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine (1.4 g, 3.63 mmol, 1 eq) was dissolved in MeOH (20 ml) and degassed for 30 min with nitrogen. 20% Pd—(OH)2 (200 mg) was added and hydrogenation was carried out for 2 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and washed with MeOH (3×25 ml), and the filtrate was concentrated under reduced pressure. Yield: 30% (240 mg, 1.09 mmol).

Workup

  1. customdegassed for 30 min with nitrogen
  2. addition20% Pd—(OH)2 (200 mg) was added
  3. filtrationthe reaction mixture was filtered off over Celite
  4. washwashed with MeOH (3×25 ml)
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c42841d50d44e3d9072a2a62eb7f34e
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…