HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Cyanide → (+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | (+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine | HCID 70021069 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methylamine | HCID 6329 | — |
| Product | (+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine | HCID 131722392 | — |
Reaction Steps
680 mg of (+/−)-cis-8,9-dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine with 25 mg of sodium cyanide in 13 ml of 9 molar methylamine solution in ethanol are heated to 90° C. in an autoclave for 10 h. The solution is concentrated under reduced pressure and the residue is taken up in methylene chloride and extracted with water. The organic phase is dried with sodium sulfate, the solvent is removed under reduced pressure and the residue is treated with diethyl ether, filtered off with suction and dried. This gives 380 mg (56.1 % of Th.) of the title compound of m.p. 209-211° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06191138B1 |
| Source dataset | uspto-grants-2001_02 |
| ORD ID | ord-928b18d75baa4785b881fc5033d8e72a |
| Source note | uspto-grants-2001_02 |