Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(2-Aminoethyl)-1-methylpyrrolidine | HCID 98388 | — |
| Reactant | Methyl 4-[2-bromomethyl-3-(naphthalen-1-yloxy)-propenyl]-benzoate | HCID 66987041 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86640103 | HCID 86640103 | 48% |
Reaction Steps
Methyl 4-[2-bromomethyl-3-(naphthalen-1-yloxy)-propenyl]-benzoate (412 mg, 1 mmol) was dissolved acetonitrile (5 ml) in a 100 ml vessel at 0° C., and thereto triethylamine (0.21 ml, 1.5 mmol, 1.5 eq.) and 2-(1-methylpyrrolidin-2-yl)ethylamine (R1′″NH2; 0.22 ml, 1.5 mmol, 1.5 eq.) were added while stirring. The resulting mixture was heated from 0° C. to room temperature, and then reacted for 4 hours. After the completion of reaction, the solvent was distilled off, and the residue thus obtained was extracted with ethyl ester. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 220 mg of the title compound as pale yellow oil (yield 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08053435B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-3ff10d82e5484b3c9ff5fa6c7a4e81f2 |
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| Source note | uspto-grants-2011_11 |
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