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

HRID 1825647Notes

Reaction equation

HRID 1825647 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.N>CO.[Pd]>[N:10]1([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 252224-(4-Nitrophenyl)morpholine

Product 1

HCID 75655Benzenamine, 4-(4-morpholinyl)-Yield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

4-(4-Nitrophenyl)morpholine (10.3 g, 49.5 mmol;) (Lancaster Synthesis) was suspended in methanol (130 ml) and 2 M ammonia in methanol (70 mL) and 5% palladium on carbon (100 mg) was added. The mixture was hydrogenated on a Paar apparatus (50 psi) for 1 h. The reaction was allowed to cool, the catalyst was filtered and the solution was concentrated in vacuo. The crude solid was recrystallized from ethyl acetate/hexane to give 4-(4-morpholinyl)aniline as a light purple solid (6.2 g, 70% yield, mp 132-133° C.). GC/MS (EI, M+) m/Z=178.

Workup

  1. temperatureto cool
  2. filtrationthe catalyst was filtered
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3bcc471a8604f40907675605ea23529
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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