Water → 5,7-Dimethyl-8-methoxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene hydrochloride

HRID 2051429Notes

Reaction equation

HRID 2051429 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]2[C:5]=1[CH:6]1[CH:11]([CH:12]2[NH:19][CH3:20])[CH2:10][CH2:9][CH2:8][CH2:7]1.CI.O.[CH:24](Cl)(Cl)[Cl:25]>CN(C)C=O>[ClH:25].[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:24])=[C:13]2[C:5]=1[CH:6]1[CH:11]([CH:12]2[NH:19][CH3:20])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 151572475,7-Dimethyl-8-hydroxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene

Product 1

HCID 198334725,7-Dimethyl-8-methoxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.16 Gram of 60% sodium hydride was added to a dimethylformamide solution containing 0.42 g of 5,7-dimethyl-8-hydroxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene in 5 ml of dimethylformamide, followed by stirring at room temperature for 30 minutes. Then, to the mixture was added 0.13 ml of methyl iodide, followed by stirring at the same temperature for 30 minutes. Water was added to the reaction mixture and extraction was carried out with chloroform. The chloroform layer was dried with magnesium sulfate and then the solvent was removed by concentration. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4), then was dissolved in ethanol and converted to a hydrochloride with saturated hydrochloric acid gas-ethanol solution, which was recrystallized from ethanol to obtain 0.1 g of 5,7-dimethyl-8-methoxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene hydrochloride.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. dry with materialThe chloroform layer was dried with magnesium sulfate
  3. customthe solvent was removed by concentration
  4. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4)
  5. dissolutionwas dissolved in ethanol
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-745e4605c73542bfb5bff251c28a794e
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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