Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
P-Chloroacetophenone → N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | P-Chloroacetophenone | HCID 7467 | — |
| 반응물 | 3-Methoxyacetophenone | HCID 11460 | — |
| 반응물 | Deuterium | HCID 24523 | — |
| 반응물 | Sodium cyanoborohydride | HCID 5003444 | — |
| 반응물 | 3-(4-Chlorophenyl)butan-1-amine | HCID 12847657 | — |
| 반응물 | 3-Methyl-3-(4-chlorophenyl)cinnamonitrile | HCID 69709423 | — |
| 촉매 | Titanium isopropoxide | HCID 11026 | — |
| 촉매 | Palladium hydroxide | HCID 9942167 | — |
| 용매 | Acetic Acid | HCID 176 | — |
| 생성물 | N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine | HCID 22011060 | — |
반응 단계
In a similar fashion, 4-chloroacetophenone was used to prepare 3-methyl-3-(4-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(4-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-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 5B/5C as an oil; m/z (rel. int.) 317 (M+, 12), 302 (74), 210 (2), 182 (4), 164 (12), 135 (100), 121 (25), 103 (40), 91 (19), 77 (28).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06211244B1 |
| 출처 데이터셋 | uspto-grants-2001_04 |
| ORD ID | ord-199db1daa182478cb2e4719b45613e1c |
| 출처 메모 | uspto-grants-2001_04 |