(3,4-Dinitrophenyl)(morpholino)methanone → 4-(3,4-Dinitrobenzyl)morpholine

HRID 1622430Notes

Reaction equation

HRID 1622430 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=O)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:13][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone

Product 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholineYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3,4-Dinitro-benzyl)-niorpholme (2.815 kg, 10.53 mol, 1.O wt) and methanol (12.00 L, 4.3 vol) were charged to a flask under nitrogen and heated to 65 to 7O° C. The temperature was maintained until complete dissolution. The mixture was then cooled to and aged at 0 to 5° C. for 1 hour. The solids were isolated by filtration. The filter-cake was washed with methanol (2×1.50 L, 2×0.5 vol) and dried under vacuum at 35 to 45° C. to give 4-(3,4-dinitro-benzyl)-morpholine (2.353 Kg, 83.5% based on input Stage 2, 82.5% overall yield based on total input Stage 1 material) as a yellow solid.

Workup

  1. temperatureheated to 65 to 7O° C
  2. temperatureThe temperature was maintained until complete dissolution
  3. temperatureThe mixture was then cooled to and
  4. customThe solids were isolated by filtration
  5. washThe filter-cake was washed with methanol (2×1.50 L, 2×0.5 vol)
  6. customdried under vacuum at 35 to 45° C.

Sources & evidence

ORD record
ord-43825e893af749caa0f47afac9c45143
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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