HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(3-Benzylpyrrolidin-1-yl)-2-methyl-6-phenoxyquinoline hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Benzylpyrrolidine | HCID 3829791 | — |
| Reactant | 4-Chloro-2-methyl-6-phenoxyquinoline | HCID 16767289 | — |
| Solvent | Glycol monoethyl ether | HCID 8076 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | 4-(3-Benzylpyrrolidin-1-yl)-2-methyl-6-phenoxyquinoline hydrochloride | HCID 68777799 | — |
Reaction Steps
4-Chloro-2-methyl-6-phenoxyquinoline (0.2 g; see Preparation 3 above) and 3-benzyl-pyrrolidine (0.3 g) in 2-ethoxyethanol (4 mL) were heated in a microwave to 200° C. for 20 minutes. The mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, dried (MgSO4), filtered and evaporated. The residue was purified by preparative HPLC, the relevant fractions combined and evaporated to give a clear oil which was acidified with concentrated hydrochloric acid and then evaporated. Trituration with ether gave the title compound as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759348B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-76dbcac6c7f54639a52933205e94a590 |
| Source note | uspto-grants-2014_06 |