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

HRID 1639624Notes

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

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%). (LC/MS (basic method): Rt 2.80, [M+H]+ 268).

Workup

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

Sources & evidence

ORD record: ord-7cffcf409b9e47be96a11625a1f28821
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110573B2

Reaction notes

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