N,N-Dibenzyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine → 2-[1-(Pyridin-4-yl)piperidin-4-yl]ethan-1-amine

HRID 1193301Notes

Reaction equation

HRID 1193301 reaction equation
C([N:8](CC1C=CC=CC=1)[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>C(O)C>[N:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:16][CH2:15]2)=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 66799257N,N-Dibenzyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine

Product 1

HCID 220278212-[1-(Pyridin-4-yl)piperidin-4-yl]ethan-1-amineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-Dibenzyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine (1.4 g, 3.63 mmol, 1 eq) was dissolved in ethanol (80 ml) and degassed for 30 min with nitrogen. 20% Pd(OH)2 (800 mg) was added and hydrogenation was carried out for 48 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and washed with ethanol (200 ml), and the filtrate was reduced under reduced pressure. Yield: 94% (700 mg, 3.41 mmol).

Workup

  1. customdegassed for 30 min with nitrogen
  2. addition20% Pd(OH)2 (800 mg) was added
  3. filtrationthe reaction mixture was filtered off over Celite
  4. washwashed with ethanol (200 ml)

Sources & evidence

ORD record
ord-90fe187226834befa542f12de65062aa
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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