Boron trifluoride etherate → 4-(3,4-Dinitrobenzyl)morpholine

HRID 1622417Notes

Reaction equation

HRID 1622417 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].[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[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

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone

Product 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a mixture of (3,4-dinitro-phenyl)-morpholin-4-yl-methanone (1 mol. eq.) in dry tetrahydrofuran (THF) (25 vol.), at 0-5° C., was added NaBH4 (2 mol. eq.) followed drop-wise by BF3-Et2O (1.01 mol. eq.) so as to maintain the temperature at 0-5° C. The mixture was then stirred at ambient temperature for 3 hours and then quenched through addition of methanol. The mixture was then reduced in vacuo, partitioned between ethyl acetate and saturated aqueous NaHCO3. The mixture was stirred rapidly for 30 minutes before separating the layers. The organic layer was washed successively with water and brine before being reduced in vacuo. The product was crystallised from methanol to give 4-(3,4-dinitro-benzyl)-morpholine (85%).

Workup

  1. customquenched through addition of methanol
  2. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  3. stirringThe mixture was stirred rapidly for 30 minutes
  4. custombefore separating the layers
  5. washThe organic layer was washed successively with water and brine
  6. customThe product was crystallised from methanol

Sources & evidence

ORD record
ord-bfc12de631a44012b5bf4b4c188b95cf
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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