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

HRID 1091390Notes

Reaction equation

HRID 1091390 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>[Pd].O>[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 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 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 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

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 mixture of tetrahydrofuran (20 ml), methanol (40 ml) and water (7 ml) was added 10% palladium on carbon (wet, 300 mg) and 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%) as 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-be01f6be38a748f6833c2b87f8afc5e0
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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