Methanol → Benzenamine, 4-(4-morpholinyl)-

HRID 1665657Notes

Reaction equation

HRID 1665657 reaction equation
[Cl-].[NH4+].CO.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([O-])=O>O.C1COCC1.[Zn]>[N:14]1([C:11]2[CH:10]=[CH:9][C:8]([NH2:5])=[CH:13][CH:12]=2)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

Participants

7

Reactant 3

HCID 887MethanolHCID 252224-(4-Nitrophenyl)morpholineHCID 25517Ammonium Chloride

Product 1

HCID 75655Benzenamine, 4-(4-morpholinyl)-Yield 77.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (1.2 g, 23.0 mmol) in water (4.5 mL) then MeOH (9 mL) were added to a stirred solution of 4-(4-nitro-phenyl)-morpholine (480 mg, 2.3 mmol) in THF (9 mL). Zinc powder (1.2 g, 18.4 mmol) was then added portion wise and the resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was filtered over celite and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated to afford 316 mg (77%) of 4-morpholin-4-yl-phenylamine. 1H NMR: (DMSO-d6): δ 6.7 (m, 2H), 6.5 (m, 2H), 4.6 (s, 2H), 3.7 (t, 4H), 2.8 (t, 4H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-982537f6a33b4c5fa2ee47e9edea3e57
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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