Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloro-5-methylphenylboronic Acid (contains varying amounts of Anhydride) | HCID 17750235 | — |
| Reactant | 3-(S)-benzyl-1-(4-bromobenzyl)-piperazine | HCID 57849462 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 57849521 | HCID 57849521 | 99% |
Reaction Steps
1 g of 3-(S)-benzyl-1-(4-bromo-benzyl)-piperazine were combined with 1.5 equiv. of 2-chloro-5-methylphenyl boronic acid, 0.05 equiv. of tetrakis(triphenylphosphine)palladium(0), 6 equiv. of 2M aqueous sodium carbonate solution, toluene and ethanol. The reaction mixture was heated at 85° C. under nitrogen overnight. The reaction mixture was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 1.1 g of the title compound. Yield 99% ES MS (+) m/z 391.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07595397B2 |
|---|
| Source dataset | uspto-grants-2009_09 |
|---|
| ORD ID | ord-e20280a2100c4a17b8e310abb405b1b3 |
|---|
| Source note | uspto-grants-2009_09 |
|---|
