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

HRID 1946269Notes

Reaction equation

HRID 1946269 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-f3406c68b9ac4662bcdbe43655a4c0fd
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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