HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → 5,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one | HCID 13729188 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5,11-Dihydro-11-[1-oxo-6-(1-piperidinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one | HCID 13729189 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04724236 |
| Source dataset | uspto-grants-1988_02 |
| ORD ID | ord-301ed65de99248bebe2bd6e6ac674570 |
| Source note | uspto-grants-1988_02 |