4-(3-Fluoro-4-nitrophenyl)morpholine → 2-Fluoro-4-(4-morpholinyl)benzenamine

HRID 1266312Notes

Reaction equation

HRID 1266312 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 222807594-(3-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 114810032-Fluoro-4-(4-morpholinyl)benzenamineYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(3-fluoro-4-nitrophenyl)morpholine (6.01 g, 26.59 mmol) and a catalytic amount of palladium on carbon (10%) were suspended in 100 mL methanol in a Parr flask. The reaction mixture was placed on the Parr Hydrogenator at 60 psi for 2 H. The reaction mixture was passed through a Celite pad and the filtrate was concentrated under reduced pressure to give 4.50 g of N-(3-fluoro-4-aminophenyl)morpholine an off-colored solid. 1HNMR (DMSO-d6) δ: 6.73 (t, 1H, J=9.34), 6.28 (m, 2H), 3.64 (bt, 4H, J=4.58 Hz), 2.76 (bt, 4H, J=4.58 Hz). ESI mass spectrum analysis m/z (relative intensity) 197 (M+H, 100). 19FNMR (DMSO-d6) δ: −124.455.

Workup

  1. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-61e311ecf47845f58104b3927128056f
Source dataset
uspto-grants-2003_04
Patent number
US06548512B1

Reaction notes

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