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

HRID 1946262Notes

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-12ecf77339a34e9aba3241428f498c06
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399442B2

Reaction notes

Loading…