Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 22393623 | HCID 22393623 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 22393781 | HCID 22393781 | 6.7% |
Reaction Steps
In a nitrogen atmosphere, 1-(4-cyano-5-methyl-4-[(2,5-dibromo)-3-thienyl]hexyl)-4-[2-(3-cyanophenoxy) ethyl] piperazine (145 mg) was dissolved in a mixed solvent of dimethylformamide (10 mL)/water (0.1 mL) of zinc cyanide (57.3 mg) and 1,1′-bis(diphenylphosphino)ferrocene (13.5 mg). Palladium-dibenzylidene acetone complex (8.9 mg) was added thereto, the atmosphere of the mixture was replaced 3 times with nitrogen, and then the solution was stirred at 120° C. for 4 hours. Water, diethyl ether and an aqueous ammonia were added thereto, to separate the organic layer. The resulting organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. After filtering off the drying agent, the filtrate was evaporated, and the residue was purified by LC-MS (ODS column; acetonitrile/water system), to give the title compound as a yellow oil (8 mg, 6.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06906072B1 |
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| Source dataset | uspto-grants-2005_06 |
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| ORD ID | ord-e9c3135a0ea5408c82445d023d9453bd |
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| Source note | uspto-grants-2005_06 |
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