HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine, hydrochloride → N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acid | HCID 18332970 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide | HCID 10585665 | 67.6% |
Reaction Steps
To the mixed solution of 2-oxo-1,2,3,4-tetrahydro-3-quinolineacetic acid (810 mg) in THF (10 ml) and acetonitrile (10 ml), WSC (1.15 g), HOBt (610 mg), dimethylamine hydrochloride (650 mg) and triethylamine (1.67 ml) were added subsequently, which was stirred at room temperature overnight. Water was added to the reaction mixture, which was extracted with a mixed solvent of ethyl acetate-THF (1:1). The organic layer was washed subsequently with 0.1N aqueous hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated to obtain the entitled compound (620 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329389B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-da3c7ded1c084ffcaa59d359b91b513d |
| Source note | uspto-grants-2001_12 |