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

HRID 1431221Notes

Reaction equation

HRID 1431221 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)([O-])=O>CCOC(C)=O>[O:19]1[CH2:20][CH2:21][N:16]([C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:9][C:4]=2[NH2:1])[CH2:17][CH2:18]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′-(2-nitro-1,4-phenylene)dimorpholine (5.6 g, 19 mmol) in EtOAc (90 mL) 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 the reaction was cooled to rt and a precipitate formed. The precipitate was collected and washed with 1N NaOH (40 mL), water (50 mL) and brine (50 mL) and dried under vacuum overnight. After this time the solid was dissolved in EtOAc (200 mL) and washed with 1N NaOH (30 mL) and brine (50 mL), dried over magnesium sulfate, filtered and evaporated in vacuo to give 2,5-dimorpholinoaniline.

Workup

  1. temperatureat reflux for 90 min
  2. temperatureAfter this time the reaction was cooled to rt
  3. customa precipitate formed
  4. customThe precipitate was collected
  5. washwashed with 1N NaOH (40 mL), water (50 mL) and brine (50 mL)
  6. customdried under vacuum overnight
  7. dissolutionAfter this time the solid was dissolved in EtOAc (200 mL)
  8. washwashed with 1N NaOH (30 mL) and brine (50 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-efbaf7a11df84c4ab292d578e4104e70
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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