Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 57934092 | HCID 57934092 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57934190 | HCID 57934190 | 56.6% |
Reaction Steps
To a solution of ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{4-[methyl(2-piperidin-1-ylethyl)amino]benzyl}amine (108 mg) in dichloromethane (5 ml) was added boron tribromide (1.0 M solution in dichloromethane) (1.0 ml) on an ice bath. The solution was stirred for 30 minutes while warming to room temperature, then methanol (2 ml) was added thereto on an ice bath. A saturated aqueous solution of sodium bicarbonate was added thereto, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The resulting residue was purified by NH silica gel column chromatography (chloroform-methanol system) to provide the title compound (58 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399520B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-91b20d2062be4e18a10d53df4a3049b3 |
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| Source note | uspto-grants-2013_03 |
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