Hydrochloric Acid → HCID 131718437, compound

HRID 1109105Notes

Reaction equation

HRID 1109105 reaction equation
[ClH:1].C[O:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@H:9]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl>Br>[ClH:1].[ClH:1].[O:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][N:12]2[C@@H:13]3[C@@H:9]([C:8]4[CH:7]=[CH:6][CH:5]=[C:4]([OH:3])[C:16]=4[CH2:15][CH2:14]3)[CH2:10][CH2:11]2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131718439HCID 131718439, compound

Product 1

HCID 131718437HCID 131718437, compoundYield 165.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6.28 g (0.016 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-morpholinoethyl)-1H-benzo[e]indole hydrochloride were dissolved in 0.51 of 48 percent aqueous HBr, boiled under reflux for 4 hours and then concentrated, whereupon the residue was dissolved in water. The solution was neutrallized by adding firstly solid Na2SO3 and then saturated aqueous NaHCO3 solution. The mixture was extracted three times with CH2Cl2, the organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered, the filtrate was concentrated and the residue was chromatographed over 0.27 kg of silica gel with methylene chloride/methanol (4:1). The product (4.8 g) was dissolved in 150 ml of ethanol. 6 ml (0.035 mol) of 21 percent ethanolic HCl solution were added dropwise thereto and the mixture was stirred at room temperature for 4 hours, whereby crystals separated. Recrystallization from ethanol gave 4.97 g (82%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(2-morpholinoethyl)-1H-benzo[e]indol-6-ol dihydrochloride as white crystals with m.p. 230°-275° (dec.).

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated, whereupon the residue
  3. dissolutionwas dissolved in water
  4. additionby adding firstly solid Na2SO3
  5. extractionThe mixture was extracted three times with CH2Cl2
  6. washthe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customthe residue was chromatographed over 0.27 kg of silica gel with methylene chloride/methanol (4:1)
  11. dissolutionThe product (4.8 g) was dissolved in 150 ml of ethanol
  12. customwhereby crystals separated
  13. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2ae646dbae784720b2c7f024259cd967
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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