HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamate | HCID 60200429 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile | HCID 60200920 | 99% |
Reaction Steps
To a solution of 1,1-dimethylethyl {1-[2-(7-cyano-2-oxo-1(2H)-quinolinyl)ethyl]-4-piperidinyl}carbamate (1.1 g, 2.8 mmol) in chloroform (15 ml) was added 4N HCl in 1,4-dioxane (15 ml) and the reaction stirred at rt for 45 mins. Toluene was then added and the solution was evaporated, dissolved in MeOH and treated with Amberlyst A21 basic resin for 30 m until pH of the solution is basic. The resine was filtered off and the solvent removed; the residue was subjected to column chromatography on silica gel eluting with 0-15% 2M ammonia in methanol-DCM to afford the desired compound (0.82 g, 99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-d4187a76de6a4a5d8b5fa3cfa26cc2a2 |
| Source note | uspto-grants-2011_12 |