HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-[[2-(3-Butoxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Butyl bromide | HCID 8002 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-[[2-(3-hydroxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide | HCID 59596831 | — |
| Reactant | HCID 178506587 | HCID 178506587 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-[[2-(3-Butoxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochloride | HCID 66591202 | 50% |
Reaction Steps
A solution of 2-[[2-(3-hydroxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide (1.0 g 3.3 mmol), 1-bromobutane (0.43 ml, 4 mmol), potassium carbonate (680 mg 5 mmol), potassium iodine (50 mg, 0.3 mmol), in DMF (30 ml) was refluxed for 16 h. After filtration over celite pad, the solution was evaporated from the solvent and the crude oil obtained purified by preparative HPLC. The hydrochloride salt was prepared by adding HCl 1N in AcOEt to the free amine dissolved in ethyl ether. After filtration, 690 mg (50% yield) the title compound was obtained as a white solid of 99% purity.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07855227B2 |
| Source dataset | uspto-grants-2010_12 |
| ORD ID | ord-8885e7c0d9a8486eac642bb50d8f14f1 |
| Source note | uspto-grants-2010_12 |