1-Phenethylpiperazine → 1-Benzofuran-7-yl-4-phenethyl-piperazine; hydrochloride

HRID 224

Reaction equation

HRID 224 reaction equation
Brc1cccc2ccoc12.c1ccc(CCN2CCNCC2)cc1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)cc1

Participants

7

Reactant 2

HCID 792141-PhenethylpiperazineHCID 1136287-Bromo-1-benzofuran

Product 1

HCID 100180471-Benzofuran-7-yl-4-phenethyl-piperazine; hydrochlorideYield 62.12%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A dried Radley tube was charged with rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (6.32 mg, 10.15 µmol), Tris(dibenzylideneacetone)dipalladium(0) (4.65 mg, 5.08 µmol) and Sodium tert- butoxide (34.1 mg, 0.36 mmol). Argon atmosphere was introduced and toluene (3ml) was added followed by 7-bromobenzofuran (50mg, 0.25 mmol) and 1-phenethylpiperazine (48.3 mg, 0.25 mmol). The reaction mixture was heated at reflux over night. 2010-03-25 The reaction mixture was filtered, concentrated and purified by flash chromatography (Isolute Si 10g, heptane: ethyl acetate; 4:1) to give 1-(benzofuran-7-yl)-4-phenethylpiperazine (48.3 mg, 62.1 %)

Sources & evidence

ORD record
ord-8cfc6888cfb048a3bbd7a788345f4499
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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