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

HRID 1063500Notes

Reaction equation

HRID 1063500 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:14]([O-])=O>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[NH2:14]

Participants

4

Reactant 1

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

Product 1

HCID 114810032-Fluoro-4-(4-morpholinyl)benzenamineYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Fluoro-4-morpholinonitrobenzene (1.80 g) was dissolved in methanol (100 mL) and 10% Pd/C (94 mg) was added. The mixture was placed in a hydrogenator (45 psi) for 2.5 h. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated to give 1.51 g solid. 1H NMR (CDCl3) δ 6.76-6.54 (m, 3H), 3.84 (t, 4H), 3.45 (bs, 2H), 3.02 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 197.1 (M+H, 100).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8979353764b84b0a83356982ceb49837
Source dataset
uspto-grants-2005_11
Patent number
US06965036B2

Reaction notes

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