HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzaldehyde → (R,R)-N-[4-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzaldehyde | HCID 6996 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | (R)-1-(3-Methoxyphenyl)ethylamine | HCID 7020759 | — |
| Reactant | 4-(2-Chlorophenyl)butan-2-one | HCID 18551300 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | (R,R)-N-[4-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine | HCID 54475061 | — |
Reaction Steps
In a similar fashion an equal molar amount of 4-(2-chlorophenyl)-2-butanone, prepared from o-chlorobezaldehyde, (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-(2-chlorophenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 4T; m/z (rel. int.) 317 (M+, 3), 302 (16), 178 (62), 135 (100), 125 (15), 105 (10), 91 (6), 77 (8).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06211244B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-dd215f8e392c43648bdf3b0991076bd9 |
| Source note | uspto-grants-2001_04 |