HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethylcarbamoyl chloride → 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl diethylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethylcarbamoyl chloride | HCID 6916 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dehydroaripiprazole | HCID 10114519 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2-yl diethylcarbamate | HCID 57501580 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of dehydro-aripiprazole (1.50 g, 3.36 mmol), triethylamine (1.03 mL, 7.39 mmol), diethyl carbamoyl chloride (1.02 mL) were combined in tetrahydrofuran (30 mL). This was then heated to 100° C. for 6 hours by microwave. The reaction was quenched with water (50 mL) and extracted with dichloromethane (2×100 mL). The combined organics were dried (MgSO4) and concentrated. The crude product was purified by column chromatrography on silica eluting with ethyl acetate to 20% tetrahydrofuran/ethyl acetate to give the product. The product was then triturated with heptane to remove aliphatic impurities and then dried to give Compound-334 (1.54 g) as a light brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09072788B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-514b1cdb2fc8441a9eedfe821d093bc7 |
| Source note | uspto-grants-2015_07 |