Ammonium formate → N2,N2-dimethyl-N1-(4-((2S)-morpholin-2-yl)phenyl)glycinamide

HRID 424444Notes

Reaction equation

HRID 424444 reaction equation
[CH3:1][N:2]([CH3:27])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[O:18][CH2:17][CH2:16][N:15]([C@@H](C3C=CC=CC=3)C)[CH2:14]2)=[CH:9][CH:8]=1)=[O:5].C([O-])=O.[NH4+]>O1CCCC1.CO.O.[Pd]>[CH3:1][N:2]([CH3:27])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C@@H:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:11][CH:12]=1)=[O:5]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 66594605N2,N2-dimethyl-N1-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)glycinamide

Product 1

HCID 66594891N2,N2-dimethyl-N1-(4-((2S)-morpholin-2-yl)phenyl)glycinamideYield 96%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N2,N2-dimethyl-N1-{4-[(2S)-4-((1R)-1-phenylethyl)morpholin-2-yl]phenyl}glycinamide (0.91 g, 2.5 mmol) and ammonium formate (0.79 g, 12.5 mmol) in tetrahydrofuran (20 ml), methanol (40 ml) and water (7 ml) was added 10% palladium on carbon (wet, 300 mg) and the mixture was stirred at 95° C. for 3 hours. After filtration, the solvent was removed in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give N2,N2-dimethyl-N1-{4-[(2S)-morpholin-2-yl]phenyl}glycinamide (0.63 g, 96%) a colorless oil.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6bff4777ed2042dbbe60bc6dffe6fccf
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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