Benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → N-methoxy-N-methylpiperidine-4-carboxamide

HRID 453658Notes

Reaction equation

HRID 453658 reaction equation
[CH3:1][O:2][N:3]([CH3:22])[C:4]([CH:6]1[CH2:11][CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8][CH2:7]1)=[O:5]>CCO.[Pd].[C]>[CH3:1][O:2][N:3]([CH3:22])[C:4]([CH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)=[O:5]

Participants

4

Reactant 1

HCID 22574154Benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Product 1

HCID 22405751N-methoxy-N-methylpiperidine-4-carboxamideYield 92.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (5.0 g, 16.32 mmol) in absolute EtOH (75 mL) was charged with 10% Pd-carbon (500 mg). The flask was evacuated and backfilled with hydrogen. The mixture was stirred for 60 h under 1 atmosphere of hydrogen (latex balloon). The catalyst was removed by filtration and the filtrate concentrated and azeotroped twice with MeOH (50 mL) to give the title compound (2.6 g, 15.10 mmol, 92% yield) as a pale yellow oil. LC-MS: (Waters Sunfire C18 4.6 mm×30 mm). 313.20, [M+H]; tR=0.12 min; 2 min gradient from 10/90/0.1 MeOH/H2O/TFA to 90/10/0.1 MeOH/H2O/TFA at 5 mL/min flow rate. 1H-NMR (400 MHz, CDCl3) δ ppm 3.65 (3H, s), 3.12 (3H, s), 3.08 (2H, dt, J=12.59, 3.27 Hz), 2.76 (1H, s), 2.61 (2H, td, J=12.21, 3.27 Hz), 1.57-1.69 (5H, m).

Workup

  1. customThe flask was evacuated
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated
  4. customazeotroped twice with MeOH (50 mL)

Sources & evidence

ORD record
ord-075e021073b34709935be9de80ee20cf
Source dataset
uspto-grants-2013_07
Patent number
US08492550B2

Reaction notes

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