Methyl iodide → HCID 12361861, compound

HRID 461564Notes

Reaction equation

HRID 461564 reaction equation
[H-].[Na+].CN(C)C1CC2C3C(=CC=CC=3C)NC=2CC1.CI.Cl.[CH3:23][N:24]([CH3:40])[CH:25]1[CH2:37][C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][C:34]=3[CH3:38])[N:29]([CH3:39])[C:28]=2[CH2:27][CH2:26]1>O.CN(C)C=O>[CH3:40][N:24]([CH3:23])[CH:25]1[CH2:37][C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][C:34]=3[CH3:38])[N:29]([CH3:39])[C:28]=2[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12361831N,N,5-Trimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amineHCID 12361862HCID 12361862, compound

Product 1

HCID 12361861HCID 12361861, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 1 g. of sodium hydride in 20 ml. of dimethylformamide was added 9.5 g. of 3-(dimethylamino)-5-methyl-1,2,3,4-tetrahydrocarbazole (Example 245A) in 100 ml. of dimethylformamide. The mixture was stirred for one hour, 5.9 g. of methyl iodide was added to the resulting clear solution in one portion, and the solution was heated for two hours on a steam bath, stirred at room temperature for one hour, diluted in 300 ml. of water and left stand for eighteen hours. The resulting solids were filtered, the filtrate was extracted with ether, the ether extract was washed with water and dried over magnesium sulfate and evaporated to dryness. The residue was combined with the solids, dissolved in ether and treated with hydrogen chloride in ethyl alcohol to give, on recrystallization from water, 3.5 g. of 3-(dimethylamino)-5,9-dimethyl-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 318°-320° C.

Workup

  1. temperaturethe solution was heated for two hours on a steam bath
  2. stirringstirred at room temperature for one hour
  3. additiondiluted in 300 ml
  4. filtrationThe resulting solids were filtered
  5. extractionthe filtrate was extracted with ether
  6. extractionthe ether extract
  7. washwas washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. dissolutiondissolved in ether
  11. additiontreated with hydrogen chloride in ethyl alcohol
  12. customto give, on recrystallization from water, 3.5 g

Sources & evidence

ORD record
ord-d98ccacb7daa4debb95b9a09dde196be
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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