4-(4-Morpholino-3-nitrophenyl)morpholine → 2,5-Dimorpholinobenzenamine

HRID 1431275Notes

Reaction equation

HRID 1431275 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][C:8]=2[N+:19]([O-])=O)[CH2:3][CH2:2]1>CCOC(C)=O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:9][C:8]=2[NH2:19])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 596314194-(4-Morpholino-3-nitrophenyl)morpholine

Product 1

HCID 288098152,5-Dimorpholinobenzenamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-(4-morpholino-3-nitrophenyl)morpholine (5600 mg, 19 mmol) in EtOAc was added stannous chloride, dihydrate (18 g, 95 mmol). The reaction was stirred at rt for 10 min and at reflux for 90 min. After this time LC/MS shows desired product. The reaction was cooled to rt and the precipitate was collected and washed with aq. 1N sodium hydroxide solution, water and brine and dried under vacuum overnight. After this time the solid was dissolved in EtOAc and washed with aq. 1N sodium hydroxide solution and brine, dried, filtered and evaporated in vacuo to give desired product. The filtrate was diluted with EtOAc (300 mL) and washed with aq. sodium hydroxide and brine, dried over magnesium sulfate, filtered and evaporated in vacuo to give additional desired product.

Workup

  1. temperatureat reflux for 90 min

Sources & evidence

ORD record
ord-cc629b913bd347bda79dd567222e9d5b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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