化工社化工社 化学情報印刷レポート · 研究参考用
3-Methoxyacetophenone → N-[3-methyl-3-(3-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 3-Methoxyacetophenone | HCID 11460 | — |
| 反応物 | 1-(3-Chlorophenyl)ethanone | HCID 14933 | — |
| 反応物 | Deuterium | HCID 24523 | — |
| 反応物 | Sodium cyanoborohydride | HCID 5003444 | — |
| 反応物 | 3-(3-Chlorophenyl)butan-1-amine | HCID 22011064 | — |
| 反応物 | 3-Methyl-3-(3-chlorophenyl)cinnamonitrile | HCID 69709831 | — |
| 触媒 | Titanium isopropoxide | HCID 11026 | — |
| 触媒 | Palladium hydroxide | HCID 9942167 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 生成物 | N-[3-methyl-3-(3-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine | HCID 22011052 | — |
反応手順
In a similar fashion, 3-chloroacetophenone was used to prepare 3-methyl-3-(3-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(3-chlorophenyl)propylamine. An equal molar amount of the amine, 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 1 M, 5 mmol). Work-up and chromatography afforded N-[3-methyl-3-(3-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 4Z/5A, as an oil; m/z (rel. int.) 283 (M+, 17), 268 (71), 164 (13), 135 (100), 121 (21), 105 (27), 91 (26), 77 (14).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06211244B1 |
| 出典データセット | uspto-grants-2001_04 |
| ORD ID | ord-31f2c2f44c0b438fa66f7cdff8967716 |
| 出典メモ | uspto-grants-2001_04 |