HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Chlorobenzaldehyde → N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Chlorobenzaldehyde | HCID 7726 | — |
| Reactant | 3-Methoxyacetophenone | HCID 11460 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 3-(4-Chlorophenyl)propan-1-amine | HCID 6485772 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Product | N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine | HCID 22011071 | — |
Reaction Steps
An equal molar amount of 3-(4-chlorophenyl)propylamine (prepared in a similar fashion from 4-chlorobenzaldehyde as above) 3′-methoxyacetophenone and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of I M, 5 mmol). Work-up and chromatography afforded N-[3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 6V, as an oil; m/z (rel. int.) 303 (M+, 8), 288 (91), 196 (4), 164 (10), 135 (100), 125 (61), 103 (21), 91 (21), 77 (18).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06211244B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-0d08c1404a424c6fac313457eee92acd |
| Source note | uspto-grants-2001_04 |