Methanol → (S)-4-(Morpholin-2-yl)aniline

HRID 1091375Notes

Reaction equation

HRID 1091375 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C@@H](C3C=CC=CC=3)C)[CH2:9]2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+].CO.O>O1CCCC1.[Pd]>[NH:10]1[CH2:11][CH2:12][O:13][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:9]1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2723923Ammonium formateHCID 66594463HCID 66594463, compound

Product 1

HCID 66594670(S)-4-(Morpholin-2-yl)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (2S)-2-(4-aminophenyl)-4-((1R)-1-phenylethyl)morpholine (17.45 g, 61.8 mmol) and ammonium formate (11.7 g, 185.4 mmol) in a mixture of tetrahydrofuran (180 ml), methanol (180 ml) and water (45 ml) was added 10% palladium on carbon (wet, 1.8 g) 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 4-((2S)-morpholin-2-yl)phenylamine (10.45 g, 95%) as pale yellow crystals.

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-373afb0e2b584e338c5d145424e52150
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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