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

HRID 635824
Notes
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Reaction equation

HRID 635824 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 70021069(+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

Product 1

HCID 131722392(+/-)-cis-6-[4-(N-methylaminocarbonyl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6329Methylamine
Solvent

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

  1. concentrationThe solution is concentrated under reduced pressure
  2. extractionextracted with water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. additionthe residue is treated with diethyl ether
  6. filtrationfiltered off with suction
  7. customdried

Sources & evidence

ORD record
ord-928b18d75baa4785b881fc5033d8e72a
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06191138B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes