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

HRID 1639603Notes

Reaction equation

HRID 1639603 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)-morpholin-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-416e0854c7c94d95a8b3e90f8f9b248a
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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