HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Trifluoromethyl)benzaldehyde → (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Trifluoromethyl)benzaldehyde | HCID 67990 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | (R)-1-(3-Methoxyphenyl)ethylamine | HCID 7020759 | — |
| Reactant | 4-[3-(Trifluoromethyl)phenyl]butan-2-one | HCID 13339059 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine | HCID 9819839 | — |
Reaction Steps
In a similar fashion an equal molar amount of 4-(3-trifluoromethylphenyl)-2-butanone, prepared from m-trifluoromethylbezaldehyde, (R)-1-(3-methoxyphenyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 21Y [m/z (rel. int.) 351 (M+, 2), 336 (18), 216 (4), 202 (3), 178 (45), 135 (100), 105 (13), 91(9), 77 (8)] and (S,R-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 21X.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06211244B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-c3a3e72caf154fd8a3d4a8f4f0c8ae1a |
| Source note | uspto-grants-2001_04 |