HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-Cyclohexyl-3-[2,4-dichloro-4'-(3-dimethylamino-propoxy)-biphenyl-3-ylmethyl]-pyrrolidin-2-one hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (3-Bromo-propyl)-dimethyl-amine hydrochloride | HCID 12440776 | — |
| Reactant | 3-(3-(4-Hydroxyphenyl)-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one | HCID 59299328 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Cyclohexyl-3-[2,4-dichloro-4'-(3-dimethylamino-propoxy)-biphenyl-3-ylmethyl]-pyrrolidin-2-one hydrochloride | HCID 68471915 | 65.1% |
Reaction Steps
Place 3-(3-(4-hydroxyphenyl)-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one (0.200 g, 0.478 mmol), sodium iodide (0.072 g, 0.478 mmol, and cesium carbonate (1.25 g, 3.82 mmol) in acetone (lOmL). Add 3-bromo-N,N-dimethylpropan-1-amine hydrochloride (0.194 g, 0.956 mmol) and stir at room temperature for 3 hours. Add water and extract with DCM. Dry, filter, and concentrate. Purify by silica gel to give the free base. Dissolve in DCM and add 2M HCl in ether. Concentrate to give 84 mg (33%) of the title compound as a tan solid. Mass spectrum (apci) m/z=503.3 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07713979B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-5b70c7b2402747c89b2d1b7cd14da646 |
| Source note | uspto-grants-2010_05 |