HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → 6-(2-(3-Benzylpiperidino)-1-hydroxyethyl)-1,2,3,4-tetrahydroquinolin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Hydrocarbostyril | HCID 64796 | — |
| Reactant | 3-Benzylpiperidine | HCID 114551 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 6-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one | HCID 4961790 | — |
| Reactant | 1,2,3,4-Tetrahydro-6-(2-(3-benzylpiperidino)-1-oxoethyl)quinolin-2-one | HCID 15816913 | — |
| Reactant | chloroacetyl chloride AlCl3 DMF | HCID 86751733 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 6-(2-(3-Benzylpiperidino)-1-hydroxyethyl)-1,2,3,4-tetrahydroquinolin-2-one | HCID 9885425 | — |
Reaction Steps
A solution of 36.2 g of 1,2,3,4-tetrahydro-6-(2-(3-benzylpiperidino)-1-oxoethyl)quinolin-2-one ("A"; racemate; obtainable by reaction of 1,2,3,4-tetrahydroquinolin-2-one with chloroacetyl chloride/AlCl3 /DMF to give 6-chloroacetyl-1,2,3,4-tetrahydroquinolin-2-one ("B") and subsequent reaction with (racemic) 3-benzylpiperidine in ethanol in the presence of triethylamine) in 725 ml of methanol is treated with 3.8 g of NaBH4 and then stirred at 10° for 2 hours. Customary working up (sodium hydroxide solution/dichloromethane) gives 6-(2-(3-benzylpiperidino)-1-hydroxyethyl)-1,2,3,4-tetrahydroquinolin-2-one, racemate ("C").
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05698553 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-ce163e3bd5a04c10b181e8d87c272240 |
| Source note | uspto-grants-1997_12 |