HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Iodide → 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one | HCID 11710306 | — |
| Reactant | (3-Bromo-propyl)-dimethyl-amine hydrochloride | HCID 12440776 | — |
| Product | 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt | HCID 11712810 | — |
Reaction Steps
Using the procedure to synthesize Example 12 and using reagents 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (150 mg, 0.412 mmol), (3-bromo-propyl)-dimethyl-amine hydrochloride (167 mg, 0.824 mmol), sodium iodide (62 mg, 0.412 mmol), and cesium carbonate (1.07 g, 3.30 mmol) afford the freebase of the title compound. Dissolve freebase in dichloromethane (5 mL) and add HCl in ether (2M, 0.4 mL), concentrate to give title compound (105 mg, 52%) as a yellow solid: Mass spectrum (apci) m/z=449.3 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834194B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-6dd880a8ec774983a6223b7864b974f6 |
| Source note | uspto-grants-2010_11 |