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

HRID 557

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

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+-)-CatalystHCID 4144353Palladium (II) acetateCatalystHCID 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
View source

Linked notes

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