Carbamic acid, n-[4-methyl-1-(phenylmethyl)-4-piperidinyl]-, 1,1-dimethylethyl ester → 1,1-Dimethylethyl N-(4-methyl-4-piperidinyl)carbamate

HRID 456744Notes

Reaction equation

HRID 456744 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:14][C:11]1([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 19694923Carbamic acid, n-[4-methyl-1-(phenylmethyl)-4-piperidinyl]-, 1,1-dimethylethyl ester

Product 1

HCID 196913701,1-Dimethylethyl N-(4-methyl-4-piperidinyl)carbamateYield 59.8%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

tert-Butyl (1-benzyl-4-methyl-4-piperidinyl)-carbamate obtained in Example 10-4 (1.01 g) was dissolved in methanol (20 mL), and 20% Pd(OH)2 on carbon (300 mg) was added. The mixture was stirred under hydrogen atmosphere (4 atm) at 20° C. for 2 hrs. The reaction mixture was diluted with ethyl acetate, filtered through a pad of Celite, and concentrated. The residual solid was triturated with hexane to give the title compound as white crystals (425 mg)

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated
  3. customThe residual solid was triturated with hexane

Sources & evidence

ORD record
ord-309aab3866f943229166b4be574f56bd
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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