(3,4-Dinitrophenyl)(morpholino)methanone → 4-Morpholin-4-yl methyl-benzene-1,2-diamine

Temperature

20 °C

4-(3,4-Dinitro-benzyl)-morρholine (0.800 Kg, 2.99 mol, 1.O wt), and ethanol (11.20 L, 14.0 vol) were charged to a suitable flask and stirred at 15 to 25° C. and a vacuum/nitrogen purge cycle was performed three times. 10% Palladium on carbon (10% Pd/C, 50% wet paste, 0.040 Kg, 0.05 wt wet weight) was slurried in ethanol (0.80 L, 1.O vol) and added to the reaction. The mixture was cooled to 10 to 2O° C. and a vacuum/nitrogen purge cycle was performed three times. A vacuum/hydrogen purge cycle was performed three times and the reaction was stirred under a hydrogen atmosphere at 10 to 2O° C. Reaction completion was determined by 1H NMR analysis (d6-DMSO), typically 14 to 20 hours. A vacuum/nitrogen purge cycle was performed three times and the reaction mixture was filtered through glass microfibre paper under nitrogen. The filter-cake was washed with ethanol (3×0.80 L, 3×1.O vol) and the combined filtrate and washes were concentrated to dryness under vacuum at 35 to 45° C. to give 4-morpholin-4-yl-methyl-benzene-1,2-diamine (0.61 IKg 98.6%) as a brown solid.

1. customa vacuum/nitrogen purge cycle
2. additionadded to the reaction
3. temperatureThe mixture was cooled to 10 to 2O° C
4. customand a vacuum/nitrogen purge cycle
5. customA vacuum/hydrogen purge cycle
6. stirringthe reaction was stirred under a hydrogen atmosphere at 10 to 2O° C
7. customReaction completion
8. customwas determined by 1H NMR analysis (d6-DMSO), typically 14 to 20 hours
9. customA vacuum/nitrogen purge cycle
10. filtrationthe reaction mixture was filtered through glass microfibre paper under nitrogen
11. washThe filter-cake was washed with ethanol (3×0.80 L, 3×1.O vol)
12. concentrationthe combined filtrate and washes were concentrated to dryness under vacuum at 35 to 45° C.

ORD record

ord-db1133b026b74b80995bff909b6b3d44

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778936B2