Potassium Carbonate → 1-(2-METHOXY-4-NITROPHENYL)-4-METHYLPIPERAZINE

HRID 2230117Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.C1(C)C=CC=CC=1.[Cu]Br>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-methylpiperazine (216 mg, 2.15 mmol), 2-bromo-5-nitroanisole (1 g, 4.3 mmol), potassium carbonate (447 mg, 3.23 mmol), copper (I) bromide (86.6 mg, 0.30 mmol) in pyridine (0.5 ml) and toluene (2 ml) was heated at 100° C. overnight. After cooling, the mixture was partitioned between water and ether and the aqueous phase was further extracted with ethyl acetate. The combined organic phases were dried (Na2SO4) and evaporated under reduced pressure, to give the crude product. This was purified by chromatography on silica gel, eluting with methanol and dichloromethane, to give the title compound (D34) as a yellow/brown oil (80 mg, 15%) MH+=252.

Workup

temperatureAfter cooling
customthe mixture was partitioned between water and ether
extractionthe aqueous phase was further extracted with ethyl acetate
dry with materialThe combined organic phases were dried (Na2SO4)
customevaporated under reduced pressure
customto give the crude product
customThis was purified by chromatography on silica gel
washeluting with methanol and dichloromethane

Sources & evidence

ORD record: ord-45e720f74d304a71aa8af0135a5c497a
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423717B1

Reaction notes

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