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

HRID 1047552Notes

Reaction equation

HRID 1047552 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.[H][H]>C(O)C.[Pd]>[O:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 251933104-(3,4-Dinitrobenzyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 251933094-(Morpholinomethyl)benzene-1,2-diamineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(3,4-Dinitrobenzyl)morpholine (200 mg, 0.748 mmol) and 10% Pd/C (10 mg) were suspended in ethanol (10 mL) under nitrogen. The reaction mixture's atmosphere was exchanged for hydrogen and hydrogenation continued at ambient temperature and pressure for 24 h. The vessel was purged with nitrogen, and then the mixture was filtered through Celite with an ethanol (10 mL) rinsing. The solvent was removed in vacuo and purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound in a 65% yield. 1H NMR: (400 MHz, DMSO-d6): δ 6.46 (s, 1H), 6.40 (d, 1H, J=7.6 Hz), 6.27 (d, 1H, J=7.2 Hz), 4.37 (s, 2H), 4.32 (s, 2H), 3.52 (m, 4H), 3.18 (m, 4H), 2.26 (m, 4H).

Workup

  1. customcontinued at ambient temperature
  2. customThe vessel was purged with nitrogen
  3. filtrationthe mixture was filtered through Celite with an ethanol (10 mL)
  4. washrinsing
  5. customThe solvent was removed in vacuo and purification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-50af1430a34a4f3296b9abf36baae745
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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