Hydrazine hydrate (1:1) → Benzenamine, 4-(4-morpholinyl)-

HRID 990687Notes

Reaction equation

HRID 990687 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([O-])=O.O.[NH2:17]N>C(O)C.[Pd].C(OCC)(=O)C>[N:10]1([C:5]2[CH:6]=[CH:7][C:8]([NH2:17])=[CH:9][CH:4]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 963654-(2-Nitrophenyl)morpholine

Product 1

HCID 75655Benzenamine, 4-(4-morpholinyl)-

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Intermediate 4 (3.2 g) in ethanol (60 ml) were added hydrazine hydrate (3.71 ml) and palladium on charcoal (5%, 0.1 g). The reaction was stirred for 12 h, before being diluted with ethyl acetate (60 ml). The reaction was extracted with aqueous citric acid (5%, 4×15 ml), and the combined aqueous extracts neutralised with sodium bicarbonate. The aqueous was extracted with ethyl acetate (3 ×15 ml), and the combined organic extracts washed with brine (50 ml), dried over magnesium sulphate (2 g) and the solvent removed in vacuo to yield the title compound as a light brown oil (1.16 g).

Workup

  1. extractionThe reaction was extracted with aqueous citric acid (5%, 4×15 ml)
  2. extractionThe aqueous was extracted with ethyl acetate (3 ×15 ml)
  3. washthe combined organic extracts washed with brine (50 ml)
  4. dry with materialdried over magnesium sulphate (2 g)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a0da5079df0d44d4804708b9a8fe2007
Source dataset
uspto-grants-2002_10
Patent number
US06462042B1

Reaction notes

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