HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperazine → Vortioxetine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperazine | HCID 4837 | — |
| Reactant | 1,2-Dibromobenzene | HCID 11414 | — |
| Reactant | 1-Bromo-2-iodobenzene | HCID 11415 | — |
| Reactant | 2,4-Dimethylbenzenethiol | HCID 83617 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Vortioxetine | HCID 9966051 | — |
Reaction Steps
In one embodiment, 1-1.5 equivalents of 2,4-dimethylthiophenol, piperazine, and one of 1-bromo-2-iodo benzene and 1,2-dibromo-benzene are dispersed in toluene followed by the addition of 2-5, such as 3 equivalents NaOt-Bu and 1-2 Mole-% Pd2dba3 and rac-BINAP dispersed in toluene to obtain a mixture which is refluxed for 2-10 hours, typically 3-5 hours to obtain 1-[2-(2,4-dimethyl-phenylsulfanyl)-phenyl]-piperazine. Optionally, this product may be further reacted with aqueous HBr to achieve the corresponding hydrobromic acid addition salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09095588B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-9c064b552c664fc4a468497e7c116b12 |
| Source note | uspto-grants-2015_08 |