HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (R)-1-(piperidin-3-yloxy)isoquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate | HCID 118114503 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-1-(piperidin-3-yloxy)isoquinoline | HCID 118115704 | — |
Reaction Steps
Compound 53 was treated with 4N HCl in dioxane (40 mL) at RT for 3 h. The mixture was concentrated in vacuo to give a viscous oil which was dissolved in MeCN (200 mL). To the solution was added NaHCO3 powder (2.0 g). The mixture was stirred at RT overnight. The mixture was filtered and the filtrate was concentrated. The residue was subjected to flash column chromatography with 0%-100% EtOAc in DCM and then 0%-9% MeOH in DCM to isolate (R)-1-(piperidin-3-yloxy)isoquinoline (54).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382246B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-a69c4af49733466f9e5846f3041c8538 |
| Source note | uspto-grants-2016_07 |