Methanol → N-(4-((2S)-morpholin-2-yl)phenyl)acetamide

HRID 424418Notes

Reaction equation

HRID 424418 reaction equation
C1([C@H]([N:9]2[CH2:14][CH2:13][O:12][C@@H:11]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=3)[CH2:10]2)C)C=CC=CC=1.C([O-])=O.[NH4+].O1CCCC1.CO>[Pd].O>[NH:9]1[CH2:14][CH2:13][O:12][C@@H:11]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=2)[CH2:10]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 66594393N-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)acetamide

Product 1

HCID 66594379N-(4-((2S)-morpholin-2-yl)phenyl)acetamideYield 131.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)acetamide (6.47 g, 20 mmol) and ammonium formate (6.3 g, 100 mmol) in mixture of tetrahydrofuran (136 ml), methanol (270 ml) and water (70 ml) was added 10% palladium on carbon (wet, 270 mg) and the solution 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 N-(4-((2S)-morpholin-2-yl)phenyl)acetamide (5.78 g, quant.) as an yellow 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-6b3c2f1e2e894992935e88bf27aeb62a
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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