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Piperazine → tert-butyl N-[2-chloro-5-(piperazin-1-yl)phenyl]carbamate

HRID 635
Notes
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Reaction equation

HRID 635 reaction equation
C1CNCCN1.CC(C)(C)OC(=O)Nc1cc(Br)ccc1Cl>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(C)(C)OC(=O)Nc1cc(N2CCNCC2)ccc1Cl
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 4837PiperazineHCID 57840526Tert-butyl 5-bromo-2-chlorophenylcarbamate

Product 1

HCID 57840409tert-butyl N-[2-chloro-5-(piperazin-1-yl)phenyl]carbamateYield 57.11%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
110 °C

Procedure

palladium(II) acetate (0.110 g, 0.49 mmol), BINAP (0.244 g, 0.39 mmol) and CS2CO3 (1.594 g, 4.89 mmol) were added to a mixture of [Reactants] and piperazine (2.76 g, 32.10 mmol) in toluene (10 mL), The suspension were heated to 110 °C for 16 hours, LCMS showed product mass [M+1]:312.0 at retention time RT=1.69 min (polar short purity method). Workup reaction by additional of water (10mL), extracted with EtOAc (3x20 mL), washed with brine, dried with Na2SO4, evaporated off solvent to give a residue, which was purified by isco chromatographer, eluting with 0-10% MeOH in DCM to give as a yellow solid. LCMS confirmed the target compound.

Sources & evidence

ORD record
ord-839e83634a9943b98e2511e3c8112ffb
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes