Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate → 1-(2,6-dimethylpyrimidin-4-yl)-N-methylpiperidin-4-amine

HRID 1193320Notes

Reaction equation

HRID 1193320 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([N:14](C)[C:15](=O)OCC3C=CC=CC=3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:26])[N:3]=1>CO>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:26])[N:3]=1

Participants

3

Reactant 1

HCID 66798782Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate

Product 1

HCID 470028741-(2,6-dimethylpyrimidin-4-yl)-N-methylpiperidin-4-amineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate (3.6 g, 10.169 mmol, 1.0 eq.) was dissolved in MeOH (40 ml) and degassed for 15 min with N2. Pd(OH)2 (800 mg) was then added, and hydrogenation was carried out for 4 hours at room temperature under balloon pressure. After monitoring by TLC, the reaction mixture was filtered over Celite and washed with methanol (100 ml). The filtrate was concentrated under reduced pressure and the crude product was used in the next stage without being purified further. Yield: 95% (2.12 g, 9.636 mmol)

Workup

  1. customdegassed for 15 min with N2
  2. additionPd(OH)2 (800 mg) was then added
  3. filtrationthe reaction mixture was filtered over Celite
  4. washwashed with methanol (100 ml)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customwithout being purified further

Sources & evidence

ORD record
ord-6abd554f6f9445149c13b9bc4a33761b
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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