Carbamic acid, N-[[4-methyl-1-(phenylmethyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester → tert-butyl N-((4-methylpiperidin-4-yl)methyl)carbamate

HRID 70787Notes

Reaction equation

HRID 70787 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12](CC2C=CC=CC=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].CCO>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]1([CH3:22])[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 71274855Carbamic acid, N-[[4-methyl-1-(phenylmethyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 70650847tert-butyl N-((4-methylpiperidin-4-yl)methyl)carbamateYield 103.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

20% palladium hydroxide on carbon (283 mg) was added to an EtOH (100 ml) solution of tert-butyl[(1-benzyl-4-methylpiperidin-4-yl)methyl]carbamate (2.57 g), and stirring was performed at 70° C. under a hydrogen atmosphere of medium pressure of 3 kgf/cm2 for 16 hours. After argon purge the reaction liquid was filtered through Celite and concentrated under reduced pressure to obtain tert-butyl[(4-methylpiperidin-4-yl)methyl]carbamate (1.90 g).

Workup

  1. customAfter argon purge
  2. customthe reaction liquid
  3. filtrationwas filtered through Celite
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95cc10562c0347139f23cc137aa50a58
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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