Methanol → N-Methyl-N-(4-((2S)-morpholin-2-yl)phenyl)pyridin-2-amine

HRID 424428Notes

Reaction equation

HRID 424428 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[O:20][CH2:19][CH2:18][N:17]([C@@H](C3C=CC=CC=3)C)[CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])=O.[NH4+].CO.O>O1CCCC1.[Pd]>[CH3:1][N:2]([C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2723923Ammonium formateHCID 66703976N-Methyl-N-(4-((2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl)phenyl)pyridin-2-amine

Product 1

HCID 66703969N-Methyl-N-(4-((2S)-morpholin-2-yl)phenyl)pyridin-2-amineYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N-Methyl-N-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)-phenyl)pyridin-2-amine (0.57 g, 1.5 mmol) and ammonium formate (0.48 g, 7.6 mmol) in tetrahydrofuran (15 ml)-methanol (30 ml)-water (16 ml) was added 10% palladium on carbon (wet, 200 mg) and stirred at 95° C. for one hour. After filtration, the solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give N-Methyl-N-(4-((2S)-morpholin-2-yl)phenyl)pyridin-2-amine (0.38 g, 94%) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-71a9da0574cb4043b1cad779f60221a7
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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