Benzyl 1-(6-(dimethylamino)pyridin-3-yl)piperidin-4-yl(methyl)carbamate → N,N-Dimethyl-5-(4-(methylamino)piperidin-1-yl)pyridin-2-amine

HRID 1193381Notes

Reaction equation

HRID 1193381 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15](C)[C:16](=O)OCC3C=CC=CC=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>CO>[CH3:1][N:2]([CH3:27])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([NH:15][CH3:16])[CH2:13][CH2:14]2)=[CH:7][N:8]=1

Participants

3

Reactant 1

HCID 66799303Benzyl 1-(6-(dimethylamino)pyridin-3-yl)piperidin-4-yl(methyl)carbamate

Product 1

HCID 66798603N,N-Dimethyl-5-(4-(methylamino)piperidin-1-yl)pyridin-2-amineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 1-(6-(dimethylamino)pyridin-3-yl)piperidin-4-yl(methyl)carbamate (400 mg, 1.086 mmol, 1.0 eq.) was dissolved in MeOH (10 ml) and degassed with argon. Pd(OH)2 (200 mg) was then added and hydrogenation was carried out for 3 hours. After monitoring by TLC, the reaction mixture was filtered over Celite, the filtrate was concentrated under reduced pressure and the crude product was used in the next stage without being purified further. Yield: 94% (240 mg, 1.0212 mmol)

Workup

  1. customdegassed with argon
  2. additionPd(OH)2 (200 mg) was then added
  3. filtrationthe reaction mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customwithout being purified further

Sources & evidence

ORD record
ord-f4a2f56079bf407dbde3ceb13714c4ac
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…