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

HRID 1622402Notes

Reaction equation

HRID 1622402 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>C1COCC1>[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 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3,4-dinitro-phenyl)-moφholin-4-yl-methanone (2.84 g) in dry THF (50 ml) was added NaBH4 (954 mg) followed drop-wise by BF3-Et2O (3.2 ml). The mixture was stirred at ambient temperature for 3 hours and then quenched though addition of MeOH. The mixture was reduced in vacuo, partitioned between EtOAc and water and the organic portion washed with brine, dried (MgSO4) and reduced in vacuo. The residue was purified via flash column chromatography eluting with EtOAc to give 4-(3,4-dinitro-benzyl)-morpholine (1.08 g).

Workup

  1. customquenched though addition of MeOH
  2. custompartitioned between EtOAc and water
  3. washthe organic portion washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe residue was purified via flash column chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-56ce6e8a53294651af682899efa38440
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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