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1-Benzylpiperazine → 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

HRID 222
Notes
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Reaction equation

HRID 222 reaction equation
CN(C)C(=O)c1cc2cccc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CN(C)C(=O)c1cc2cccc(N3CCN(Cc4ccccc4)CC3)c2o1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 759941-BenzylpiperazineHCID 403935587-Bromo-N,N-dimethyl-benzofuran-2-carboxamide

Product 1

HCID 596367707-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamideYield 52.15%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

The mixture of Tris(dibenzylideneacetone)dipalladium(0) (0.222 g, 0.24 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.231 g, 0.48 mmol) in dioxane (10 mL) (degassed with argon for 5 min) was heated at 95 °C under argon for 5 min . This was transferred to a flask containing 7-bromo-N,N-dimethylbenzofuran-2-carboxamide (1.3 g, 4.85 mmol), 1-benzylpiperazine (1.111 g, 6.30 mmol) and Cesium carbonate (2.212 g, 6.79 mmol) in dioxane (10 mL) (degassed with argon for 5 min). The resulting mixture was heated at 95 °C over night. After cooling, the reaction mixture was filtered, the solid washed with DCM and concentrated. The product was purified by isco (DCM:MeOH; 0-3%). A small portion was also purified by prepLC giving EN02745-79-002.

Sources & evidence

ORD record
ord-f1c56ffe105843279dcf3ce82ed9a4b2
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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