Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 3,5-Bis(trifluoromethyl)benzylamine | HCID 521099 | — |
| Reactant | 2-(Butyl-ethyl-amino)-5-trifluoromethyl-benzaldehyde | HCID 86626752 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86626753 | HCID 86626753 | 88% |
Reaction Steps
2-(Butyl-ethyl-amino)-5-trifluoromethyl-benzaldehyde (6.5 g), 3,5-bis-trifluoromethyl-benzylamine (7.52 g), acetic acid (2.04 ml) are dissolved in 1,2-dichloroethane (50 ml), and thereto is added triacetoxy sodium borohydride (10.1 g) at room temperature and the mixture is stirred for 2 hours. To the reaction solution are added 1N-aqueous sodium hydroxide solution and methylene chloride, and the mixture is separated, and the organic layer is washed with a saturated brine and 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}-butyl-ethyl-amine (10.48 g). MS (m/z): 501 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07906517B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-67820b98770d4611b8484ef27ee377ea |
|---|
| Source note | uspto-grants-2011_03 |
|---|