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2-Chlorothiophene → 1-Boc-4-(2-thienyl)piperazine

HRID 302
Notes
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Reaction equation

HRID 302 reaction equation
CC(C)(C)OC(=O)N1CCNCC1.Clc1cccs1>CCN(CC)CC.CN(C)C=O.[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>CC(C)(C)OC(=O)N1CCN(c2cccs2)CC1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 72992-ChlorothiopheneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 673439001-Boc-4-(2-thienyl)piperazineYield 0%

Reagents, catalysts & solvents 4

HCID 8471TriethylamineReagentHCID 11776TriphenylphosphineCatalyst
On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 2-chlorothiophene (0.248 mL, 2.68 mmol), tert-butyl piperazine-1-carboxylate (500 mg, 2.68 mmol), and TEA (1.123 mL, 8.05 mmol) in DMF (4 mL) was added Pd(Ph3P)4 (57.8 mg, .05 mmol). The reaction was allowed to heat at 95 °C for overnight. LCMS and TLC showed the starting material peak as well as the triphenyl phosphene ionized M+1 peak. The tryphenyl phosphene showed up at the same retention time as 2-chlorothiophene. No new peak was observed following the reaction so no purification techniques were run. MS (m+1) = not seen

Sources & evidence

ORD record
ord-37aa4a46f5494844887cf9e7ccaf1b0d
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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