Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3,5-Bis(trifluoromethyl)benzylamine | HCID 521099 | — |
| Reactant | HCID 67087230 | HCID 67087230 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86626799 | HCID 86626799 | 81.1% |
Reaction Steps
6-Trifluoromethyl-1,3-dihydro-isobenzofuran-1-ol (4.12 g) is dissolved in 1,2-dichloroethane (75 ml), and thereto are added 3,5-bis-trifluoromethyl-benzylamine (5.89 g), triacetoxy-sodium borohydride (9.0 g) and acetic acid (2.3 ml), and the mixture is stirred at room temperature for 1 hour. To the reaction solution are added a saturated aqueous sodium bicarbonate solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=7:3→1:1) to give {2-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-methanol (7.06 g). MS (m/z): 432 [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-9d8c69cfb8ea4299ae281ddfc3a00f1b |
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| Source note | uspto-grants-2011_03 |
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