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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 635824Generated: October 30, 2026

Sodium Cyanide → (+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine

https://huagongshe.com/reaction/635824

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CyanideHCID 8929—
Reactant(+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridineHCID 70021069—
SolventEthanolHCID 702—
SolventMethylamineHCID 6329—
Product(+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridineHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06191138B1
Source datasetuspto-grants-2001_02
ORD IDord-928b18d75baa4785b881fc5033d8e72a
Source noteuspto-grants-2001_02