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p-Bromoacetophenone → Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate

HRID 557
Notes
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Reaction equation

HRID 557 reaction equation
CC(=O)c1ccc(Br)cc1.CC(C)(C)OC(=O)N1CCNCC1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7466p-BromoacetophenoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21136190Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylateYield 52.48%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-Catalyst
HCID 4144353
Palladium (II) acetate
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a CEM MW vial, p-Bromoacetophenone (729 ml, 6.03 mmol),tert-Butyl 1-piperazinecarboxylate (1.684 g, 9.04 mmol),racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.375 g, 0.60 mmol),Palladium (II) acetate (0.135 g, 0.60 mmol),Cesium carbonate (3.93 g, 12.06 mmol) was taken in toluene (10 ml).The RM was subjected to MW power of 300W,temp 120°C for 45 minutes. The LCMS was checked showed the formation of required mass. Work-up: The RM was passed through hyflow bed and filtrate was evaporated and chrmatographed using Ethyl acetate hexane to obtain tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate (0.963 g, 52.5 %).

Sources & evidence

ORD record
ord-c7d1825ed35e4dffbc57a0b9b8fa9354
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes