N,N-Dibenzyl-2-(1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamine → 2-(1-(2,6-Dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamine

HRID 1193408Notes

Reaction equation

HRID 1193408 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]=[C:21]([CH3:23])[N:20]=[C:19]([CH3:24])[N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:24][C:19]1[N:18]=[C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:16][CH2:15]2)[CH:22]=[C:21]([CH3:23])[N:20]=1

Participants

4

Reactant 1

HCID 66798939N,N-Dibenzyl-2-(1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamine

Product 1

HCID 625863752-(1-(2,6-Dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamineYield 66%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of N,N-dibenzyl-2-(1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl)ethanamine (700 mg, 1.691 mmol, 1.0 eq) in MeOH (10 ml) was degassed for 30 minutes with nitrogen; 10% Pd(OH)2 (420 mg) was added and hydrogenation was carried out for 12 hours at RT. After monitoring by TLC, the reaction mixture was filtered off over Celite and washed with MeOH (100 ml). The filtrate was concentrated under reduced pressure and dried. Yield: 66% (260 mg, 1.11 mmol)

Workup

  1. filtrationthe reaction mixture was filtered off over Celite
  2. washwashed with MeOH (100 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-12ccee123b72440ba9475d657410eeaf
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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