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1-Acetylpiperazine → 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone

HRID 48
Notes
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Reaction equation

HRID 48 reaction equation
CC(=O)N1CCNCC1.COc1ccc(Br)cc1[N+](=O)[O-]>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COc1ccc(N2CCN(C(C)=O)CC2)cc1[N+](=O)[O-]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 837951-AcetylpiperazineHCID 1185334-Bromo-2-nitroanisole

Product 1

HCID 582357111-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanoneYield 1.22%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol), 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) were suspended in dioxane (20 ml) and sealed into a microwave tube. The reaction was heated to 120 °C for 90 minutes in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite with ethyl acetate (50 mL). The filtrate was evaporated to dryness. The crude product was purified by flash silica chromatography in EtOAc. Pure fractions were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (0.022 g, 1.218 %) as a brown solid.

Sources & evidence

ORD record
ord-56a1dc90e93f4e37a4c4dceba5d45c4e
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes