Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 44329321 | HCID 44329321 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 88258910 | HCID 88258910 | 94% |
Reaction Steps
Methanesulfonyl chloride (0.04 ml, 0.5 mmol) was added to a stirred solution of trans-7-hydroxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline(E3, 200 mg, 0.4 mmol) and triethylamine (0.07 ml, 0.5 mmol) in dichloromethane (5 ml) at room temperature. The mixture was stirred for 12 h and then poured onto saturated aqueous K2CO3 (10 ml) and extracted onto dichloromethane (3×10 ml). The combined extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to give an off-white solid. Chromatography on silica using 50-100% ethyl acetate /pentane as elution gradient, afforded the free base of the title compound (200 mg, 94%). The free base was treated with 1M ethereal HCl in dichloromethane to afford after evaporation the title compound as a colourless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06080752 |
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| Source dataset | uspto-grants-2000_06 |
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| ORD ID | ord-d63386781ccc4ef0bbe961af26e5c9c8 |
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| Source note | uspto-grants-2000_06 |
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