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

HRID 1193416Notes

Reaction equation

HRID 1193416 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][CH3:26])C(=O)OCC3C=CC=CC=3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:27])[N:3]=1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:25][CH3:26])[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:27])[N:3]=1

Participants

4

Reactant 1

HCID 66798660Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(ethyl)carbamate

Product 1

HCID 549395371-(2,6-dimethylpyrimidin-4-yl)-N-ethylpiperidin-4-amineYield 66%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(ethyl)carbamate (960 mg, 2.6 mmol, 1.0 eq) in MeOH (40 ml) was degassed for 15 minutes with nitrogen; Pd(OH)2 (480 mg) was added and hydrogenation was carried out for 1 hour at RT. After monitoring by TLC, the reaction mixture was filtered off over Celite and washed with MeOH (100 ml) and the filtrate was concentrated under reduced pressure and dried. Yield: 66% (400 mg, 1.709 mmol) C. Single Substance Syntheses General Method for the Synthesis of the Illustrative Compounds (H)

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
  5. customSingle Substance Syntheses General Method for the Synthesis of the Illustrative Compounds (H)

Sources & evidence

ORD record
ord-fc0f9ce8d7e04ed6847afb6e758a56eb
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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