Methanol → HCID 66704003, compound

HRID 424425Notes

Reaction equation

HRID 424425 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]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:17][CH:16]=3)[CH2:10]2)C)C=CC=CC=1.C([O-])=O.[NH4+].CO.O>O1CCCC1.[Pd]>[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]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:19][CH:20]=2)[CH2:10]1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2723923Ammonium formateHCID 66703932HCID 66703932, compound

Product 1

HCID 66704003HCID 66704003, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)-pyridin-2-amine (0.89 g, 2.5 mmol) and ammonium formate (0.78 g, 12.5 mmol) in tetrahydrofuran (15ml)-methanol (24 ml)-water (18 ml) was added 10% palladium on carbon (wet, 200 mg) and the mixture was stirred at 95° C. for one hour. 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 concentrated under reduced pressure to yield N-(4-((2S)-Morpholin-2-yl)phenyl)pyridin-2-amine (0.60 g, 94%) as a 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. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d99c8a7647c4a7185f9ad8b0827949d
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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