Hydrochloric Acid → HCID 13491595, compound

HRID 1284920Notes

Reaction equation

HRID 1284920 reaction equation
Cl.[CH3:2][N:3]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([NH:12][CH:11]=[CH:10]3)=[C:5]2[CH2:4]1.O>O1CCOCC1>[CH3:2][N:3]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([NH:12][CH2:11][CH2:10]3)=[C:5]2[CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 13491594HCID 13491594, compound

Product 1

HCID 13491595HCID 13491595, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12.5 ml (0.131 mol) of 10.5N hydrochloric acid are added dropwise to a mixture of 26 g (0.1 mol) of 8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]indole and 29.2 g (0.4 mol) of trimethylaminoborane in 150 ml of absolute dioxane at a temperature of 16° C., with stirring and in the absence of moisture. The mixture is then heated under reflux for 30 minutes and cooled to room temperature, 50 ml (0.3 mol) of 6N HCl are added and the mixture is heated under reflux once more for 15 minutes. After cooling to room temperature, 600 ml of H2O are added to the reaction mixture, the mixture is filtered over kieselguhr and, after addition of a further 600 ml of H2O, the filtrate is brought to pH 9 with 20% strength NaOH. The aqueous phase is now extracted several times with CH2Cl2 and, after drying over Na 2 SO4, the solvent is distilled off on a rotary evaporator. The oily residue is chromatographed on silica gel (silica gel 60 from E. Merck, Darmstadt) using ethyl acetate and MeOH (20:7) as the eluent.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture is heated
  4. temperatureunder reflux once more for 15 minutes
  5. temperatureAfter cooling to room temperature
  6. filtrationthe mixture is filtered over kieselguhr
  7. additionafter addition of a further 600 ml of H2O
  8. dry with materialafter drying over Na 2 SO4
  9. distillationthe solvent is distilled off on a rotary evaporator
  10. customThe oily residue is chromatographed on silica gel (silica gel 60 from E. Merck, Darmstadt)

Sources & evidence

ORD record
ord-4d4ee8e4a2d14a02b90389d50ab9aa67
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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