HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 11-Diethylaminocarbonyl-10-methyl-7-(2-propenyl)-5,6,7,8,12,12b-hexahydro-4,8-methanobenzofuro[3,2-e]pyrrolo[2,3-g]isoquinoline-1,8a-(9H)-diol hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Naloxone Hydrochloride | HCID 5464092 | — |
| Reactant | HCID 178418240 | HCID 178418240 | — |
| Reactant | HCID 178418247 | HCID 178418247 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Product | 11-Diethylaminocarbonyl-10-methyl-7-(2-propenyl)-5,6,7,8,12,12b-hexahydro-4,8-methanobenzofuro[3,2-e]pyrrolo[2,3-g]isoquinoline-1,8a-(9H)-diol hydrochloride | HCID 86754770 | — |
Reaction Steps
1.0 g (2.75 mmoles) of naloxone hydrochloride, 2.15 g (8.25 mmoles) di N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.68 g (8.25 mmoles) of CH3COONa, 1.06 g (16.2 mmoles) of zinc dust and 15 ml of glacial acetic acid were treated as described in the Example 1. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:0.5), dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The precipitate was filtered and recrystallized twice from EtOH to yield 0.95 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05981540 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-fd0f937d339041e088b45b75b4293114 |
| Source note | uspto-grants-1999_11 |