HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → HCID 18186376, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 1-(4-Bromobenzyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline | HCID 18186409 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Tri-o-tolylphosphine | HCID 80271 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 18186376 | HCID 18186376 | 49.3% |
Reaction Steps
1-(4-Bromobenzyl)-6-phenylmethoxy-2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline (0.82 g, 1.6 mmol) and piperidine (0.17 g, 1.96 mmol) are placed in a 100 ml round bottom flask containing anh. toluene (50 mL) under nitrogen. NaOtBu (0.22 g, 2.3 mmol), Pd(dba)2 (0.029 g, 2 mol %) and P(o-tolyl)3 (0.02 g, 6 mol %) are added, and the mixture heated to reflux overnight. The reaction is cooled to RT and treated with brine and ethyl ether. The organic layer is dried over MgSO4 and purified by column chromatography (SiO2, hexanes/ethyl acetate, 6:1) to yield the title compound (0.40 g, 49% yield): ES-MS (m/z) 507 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06593322B1 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-8ea45e42fd1245c1b3abb02b7b6bcd31 |
| Source note | uspto-grants-2003_07 |