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Piperazine → 4-Fluoro-2-(piperazin-1-yl)benzonitrile

HRID 318
Notes
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Reaction equation

HRID 318 reaction equation
C1CNCCN1.N#Cc1ccc(F)cc1Br>C1COCCO1.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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>N#Cc1ccc(F)cc1N1CCNCC1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 4837PiperazineHCID 1189392-Bromo-4-fluorobenzonitrile

Product 1

HCID 193671084-Fluoro-2-(piperazin-1-yl)benzonitrileYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (0) (57.2 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (78 mg, 0.12 mmol) were added to a mixture of 2-bromo-4-fluorobenzonitrile (250 mg, 1.25 mmol), Cesium carbonate (611 mg, 1.87 mmol) and Piperazine (215 mg, 2.50 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath at 90 °C 4pm. LCMS o/n shows several peaks. Larger peak corresponding to displacement of F by piperazine (MW266) than for desired product (205). Discarded

Sources & evidence

ORD record
ord-91c1aa5c02fc46a586e9f5a373b7526a
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes