Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 3,5-Bis(trifluoromethyl)benzylamine | HCID 521099 | — |
| Reactant | HCID 86626747 | HCID 86626747 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 86626748 | HCID 86626748 | 50.1% |
Reaction Steps
2-[Ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzaldehyde (3.7 g), 3,5-bis-trifluoromethyl-benzylamine (4.23 g), acetic acid (1.15 ml) are dissolved in 1,2-dichloroethane (30 ml), and thereto is added triacetoxy sodium borohydride (5.68 g) at room temperature and the mixture is stirred at room temperature overnight. To the reaction solution are added methylene chloride and a saturated aqueous sodium bicarbonate solution, and the mixture is separated, and the organic layer is washed with a saturated brine and the mixture is dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give {2-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-ethyl-(2-methoxy-ethyl)-amine (3.38 g). MS (m/z): 503 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07906517B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-6bf9be532c8a440295b448af147a24bb |
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| Source note | uspto-grants-2011_03 |
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