Ammonium formate → N,N-dimethylmorpholine-2-carboxamide

HRID 1914043Notes

Reaction equation

HRID 1914043 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:17][N:16]([CH3:18])[C:14]([CH:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1)=[O:15]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 711385114-benzyl-N,N-dimethylmorpholine-2-carboxamide

Product 1

HCID 20472122N,N-dimethylmorpholine-2-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-benzyl-N,N-dimethylmorpholine-2-carboxamide (803 mg, 3.23 mmol), ammonium formate (2.15 g, 32.3 mmol) and 10% Pd/C (400 mg) in EtOH (20 mL) was heated at 50° C. for 1 hour. After cooling to room temperature, the catalyst was filtered off, washed with EtOH. The combined filtrate and washings were concentrated, and the residue was dissolved in EtOH (20 mL). Ammonium formate (2.15 g, 32.3 mmol) and 10% Pd/C (400 mg) were added to the mixture. The mixture was heated at 50° C. for 1 hour. After cooling to room temperature, the catalyst was filtered off, washed with EtOH. The combined filtrate and washings were concentrated to afford desired product (506 mg, 98.9%) as colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe catalyst was filtered off
  3. washwashed with EtOH
  4. concentrationThe combined filtrate and washings were concentrated
  5. dissolutionthe residue was dissolved in EtOH (20 mL)
  6. temperatureThe mixture was heated at 50° C. for 1 hour
  7. temperatureAfter cooling to room temperature
  8. filtrationthe catalyst was filtered off
  9. washwashed with EtOH
  10. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-25c055a7a16c471fb048b310c0e74a8d
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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