4-(3,4-Dinitrobenzyl)morpholine → 4-(Morpholinomethyl)benzene-1,2-diamine

HRID 1622423Notes

Reaction equation

HRID 1622423 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O>C(O)C>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine

Product 1

HCID 251933094-(Morpholinomethyl)benzene-1,2-diamineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
17.5 °C

Procedure

4-(3,4-Dinitrobenzyl)morpholine (21 g, 101 mmol) was suspended in ethanol (0.9 L) and the vessel purged with nitrogen. 10% Palladium on charcoal (1.05 g) was suspended in ethanol (25 mL) and added to the substrate. The mixture was cooled in ice then the atmosphere exchanged for hydrogen. The mixture was allowed to warm to 15-20° C. and hydrogenation continued at ambient pressure for 2 days. The vessel was purged with nitrogen then the mixture was filtered through Celite, rinsing with ethanol (0.3 L) in portions. Concentration afforded the title compound (15.8 g, 97%).

Workup

  1. customthe vessel purged with nitrogen
  2. additionadded to the substrate
  3. temperatureThe mixture was cooled in ice
  4. customThe vessel was purged with nitrogen
  5. filtrationthe mixture was filtered through Celite
  6. washrinsing with ethanol (0.3 L) in portions
  7. concentrationConcentration

Sources & evidence

ORD record
ord-7d36a875aed848b0b1cdb65cbee73ad9
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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