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Formaldehyde → 5,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Formaldehyde | HCID 712 | — |
| 反応物 | Piperidine | HCID 8082 | — |
| 反応物 | 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one | HCID 13729188 | — |
| 触媒 | Cuprous chloride | HCID 62652 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 5,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one | HCID 13729189 | — |
反応手順
A mixture consisting of 9.6 g (0.03 mol) of 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 1.08 g (0.036 mol) of paraformaldehyde, 3.06 g (0.036 mol) of piperidine, 0.2 g of copper(I) chloride and 150 ml of dioxan is refluxed for 1 hour. After the reaction has ended the insoluble constituents are filtered off and the filtrate is evaporated to dryness in vacuo. The crude product is purified by column chromatography on silica gel (mobile phase: ethyl acetate, ethyl acetate+10% methanol). After recrystallisation from ethyl acetate, 2.7 g (21% of theory) of the desired compound are obtained, m.p. 197° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04724236 |
| 出典データセット | uspto-grants-1988_02 |
| ORD ID | ord-301ed65de99248bebe2bd6e6ac674570 |
| 出典メモ | uspto-grants-1988_02 |