HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-dihydroquinolin-4(1H)-one → 1-(2-(1,2,3,4-Tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-dihydroquinolin-4(1H)-one | HCID 117158 | — |
| Reactant | 4-(3,4-Dimethoxyphenyl)piperidine | HCID 545828 | — |
| Reactant | 1-(1,2,3,4-Tetrahydroquinolin-4-yl-acetyl)-4-(3,4-dimethoxyphenyl)piperidine | HCID 18986543 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Diethylethoxycarbonyl methanephosphonate | HCID 86749290 | — |
| Catalyst | HCID 178506449 | HCID 178506449 | — |
| Product | 1-(2-(1,2,3,4-Tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine | HCID 9842863 | — |
Reaction Steps
Analogously to Example 2, reduction of 1-(1,2,3,4-tetrahydroquinolin-4-yl-acetyl)-4-(3,4-dimethoxyphenyl)piperidine [obtainable by reaction of 1,2,3,4-tetrahydroquinolin-4-one with diethylethoxycarbonyl methanephosphonate, subsequent hydrogenation with H2 /Pd-C, hydrolysis of the ester present and subsequent amide formation with 4-(3,4-dimethoxyphenyl)piperidine] using lithium aluminium hydride gives 1-(2-(1,2,3,4-tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine, m.p. 235°-236° (dihydrochloride).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05495022 |
| Source dataset | uspto-grants-1996_02 |
| ORD ID | ord-ed4875e7ec314d96aca57b39afd46e81 |
| Source note | uspto-grants-1996_02 |