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1-Bromo-4-fluorobenzene → 1-Benzyl-4-(4-fluorophenyl)piperazine

HRID 343
Notes
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Reaction equation

HRID 343 reaction equation
Fc1ccc(Br)cc1.c1ccc(CN2CCNCC2)cc1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.[Na+].[Pd]>Fc1ccc(N2CCN(Cc3ccccc3)CC2)cc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 99931-Bromo-4-fluorobenzeneHCID 759941-Benzylpiperazine

Product 1

HCID 7631991-Benzyl-4-(4-fluorophenyl)piperazineYield 74.98%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Catalyst
On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 4144353
Palladium (II) acetate
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

diacetoxypalladium (12.74 mg, 0.06 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (32.8 mg, 0.06 mmol) were suspended in toluene (0.5 mL) under N2. Heated to 50C for 30 min (microwave). sodium 2-methylpropan-2-olate (109 mg, 1.13 mmol) was suspended in toluene (0.500 mL) under N2. 1-benzylpiperazine (0.099 mL, 0.57 mmol) and 1-bromo-4-fluorobenzene (0.093 mL, 0.85 mmol) were added, followed by the catalyst solution. Heated to 100C for 2h in the microwave (high abs), then rt over night. The product was purified on silica (0-25% EtOAc/heptane) Yield: 1-benzyl-4-(4-fluorophenyl)piperazine (115 mg, 75.0 %)

Sources & evidence

ORD record
ord-8809d217cb404d41bb5809dd5f95b269
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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