Chlorine monoxide → (+/-)-cis-8,9-Dimethoxy-6-[4-(methoxycarbonyl)phenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

HRID 635822Notes

Reaction equation

HRID 635822 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O(Cl)Cl.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C@H:11]1[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]=[C:18]2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24646Chlorine monoxideHCID 516892Sodium BicarbonateHCID 53911096(+/-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.8 g of (+/−)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-methoxycarbonylbenzamide are dissolved in 50 ml of acetonitrile and 1.0 ml of phoshorus oxychloride and stirred at 50° C. for 8 h. The reaction mixture is poured into 100 ml of saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is washed with sodium bicarbonate solution and water, dried with sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate/petroleum ether. This gives 660 mg (38.6% of Th.) of the title compound of m.p.: 121.5-122.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with sodium bicarbonate solution and water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-2732bf4ca39f4108845e810d14ad117f
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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