Sodium Cyanide → (+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=O)=[CH:21][CH:20]=1.[C-:29]#[N:30].[Na+]>CN.C(O)C>[CH3:29][NH:30][C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:6]2[C:5]3[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:13]3[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[N:7]=2)=[CH:24][CH:23]=1)=[O:27]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- concentrationThe solution is concentrated under reduced pressure
- extractionextracted with water
- dry with materialThe organic phase is dried with sodium sulfate
- customthe solvent is removed under reduced pressure
- additionthe residue is treated with diethyl ether
- filtrationfiltered off with suction
- customdried
Sources & evidence
- ORD record
- ord-928b18d75baa4785b881fc5033d8e72a
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06191138B1
Reaction notes
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