Methyl iodide → HCID 21555005, compound

HRID 267554Notes

Reaction equation

HRID 267554 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[C:14]3([CH3:22])[N:18]([CH2:19][CH2:20][C:8]2=1)[C:17](=[O:21])[CH2:16][CH2:15]3.[CH3:23]I>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:23])[C:9]1[C:14]3([CH3:22])[N:18]([CH2:19][CH2:20][C:8]2=1)[C:17](=[O:21])[CH2:16][CH2:15]3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3461001HCID 3461001, compound

Product 1

HCID 21555005HCID 21555005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.06 g. of about a 50% dispersion in mineral oil) is stirred under nitrogen with 5.41 g. 1,2,5,6,11,11b-hexahydro-8-methoxy-11b-methyl-3H-indolizino[8,7-b]indol-3-one [S. Wawzonek and J. D. Nordstrom, J. Med. Chem., 8, 265 (1965)] in 100 ml. dry dimethylformamide for one-half hour. The brown solution is cooled in an ice-water bath as 3.41 g. methyl iodide (1.50 ml.) is added. After one-half hour of cooling, the reaction mass is allowed to stand at about 25°C. for sixteen hours. The dimethylformamide is removed in vacuo and the residue is twice triturated with 50 ml. hexane, dissolved in chloroform and washed with water. After drying (sodium sulfate), the solvent is removed and the solid is twice recrystallized from ethyl acetate, thus affording 4.30 g. of the title compound, m.p. 164°-7°C.; λmaxCHCl3 6.02, 6.19 μ; NMR (CDCl3); δ 1.60 (singlet, 11b-methyl), 3.68 (singlet, 11-methyl), 3.83 (singlet, methoxyl) ppm.

Workup

  1. temperatureThe brown solution is cooled in an ice-water bath as 3.41 g
  2. temperatureAfter one-half hour of cooling
  3. waitto stand at about 25°C. for sixteen hours
  4. customThe dimethylformamide is removed in vacuo
  5. customthe residue is twice triturated with 50 ml
  6. dissolutionhexane, dissolved in chloroform
  7. washwashed with water
  8. dry with materialAfter drying (sodium sulfate)
  9. customthe solvent is removed
  10. customthe solid is twice recrystallized from ethyl acetate
  11. customthus affording 4.30 g

Sources & evidence

ORD record
ord-1db21c1f390644109e0444a6cd49e954
Source dataset
uspto-grants-1976_03
Patent number
US03943148

Reaction notes

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