Methyl iodide → HCID 13491948, compound

HRID 979783Notes

Reaction equation

HRID 979783 reaction equation
[CH3:1][N:2]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@@H:8]2[C@@H:3]1[CH2:4][C:5]1[C:6]3[C:19]([NH:20][CH:21]=1)=[CH:18][CH:17]=[CH:16][C:7]=32.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:24][N:20]1[C:19]2[C:6]3=[C:7]([CH:16]=[CH:17][CH:18]=2)[C@H:8]2[C@H:3]([CH2:4][C:5]3=[CH:21]1)[N:2]([CH3:1])[CH2:15][C:14]1[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10265374HCID 10265374, compound

Product 1

HCID 13491948HCID 13491948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3 g of trans-4,6,6a,7,8,12b-hexahydro-7-methylindolo[4,3-ab]phenanthridine are dissolved in 60 ml of dimethylformamide. The solution is cooled to -25°, and mixed whilst stirring with 280 mg of a 55% sodium hydride dispersion. The resultant suspension is allowed to warm to 0° over the course of 40 mins., and then 0.81 ml of methyl iodide, dissolved in 10 ml of dimethylformamide, are added in drops. The black reaction solution is stirred for a further 1 hour at 0°, and the dimethylformamide is subsequently removed under a high vacuum. The residue of evaporation is taken up in methylene chloride/methanol=95/5, extracted with water, and the combined organic phases dried, filtered and concentrated. The residue of evaporation is chromatographed on silica gel with methylene chloride/methanol=98/2 (methylene chloride 10% saturated with NH3). The title compound which crystallises from the solvent mixture used for chromatography is thus obtained. After washing with ether and subsequent drying, it melts at 184°- 185°.

Workup

  1. temperatureThe solution is cooled to -25°
  2. additionmixed
  3. temperatureto warm to 0° over the course of 40 mins
  4. additionare added in drops
  5. customthe dimethylformamide is subsequently removed under a high vacuum
  6. customThe residue of evaporation
  7. extractionextracted with water
  8. customthe combined organic phases dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue of evaporation
  12. customis chromatographed on silica gel with methylene chloride/methanol=98/2 (methylene chloride 10% saturated with NH3)
  13. customThe title compound which crystallises from the solvent mixture
  14. customis thus obtained
  15. washAfter washing with ether and subsequent drying, it melts at 184°- 185°

Sources & evidence

ORD record
ord-fe5a116a9671489cbab1b7747e065786
Source dataset
uspto-grants-1987_01
Patent number
US04634708

Reaction notes

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