Hydrochloric Acid → HCID 131718507, compound

HRID 1109164Notes

Reaction equation

HRID 1109164 reaction equation
[CH:1]1([N:6]2[C@@H:14]3[C@@H:9]([C:10]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[C:11]=4[CH2:12][CH2:13]3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:21]>Br>[ClH:21].[CH:1]1([N:6]2[C@@H:14]3[C@@H:9]([C:10]4[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:11]=4[CH2:12][CH2:13]3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131718506HCID 131718506, compound

Product 1

HCID 131718507HCID 131718507, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1.8 g (0.0066 mol) of rac-cis-3-cyclopentyl-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.2 l of 48% aqueous HBr and boiled under reflux for 1 hour. The mixture was cooled and concentrated, whereupon 100 ml of an aqueous NaHCO3 solution and a small amount of 2N NaOH solution were added thereto, the mixture was extracted three times with CH2Cl2 and the extracts were dried with MgSO4, filtered and concentrated. The brown crystals (1.7 g) were dissolved in 30 ml of ethanol. 1.3 ml (0.0075 mol) of 5.8N ethanolic HCl solution were added dropwise thereto and the mixture was stirred at room temperature for 1 hour and at 0° for 1 hour. The separated crystals were filtered off under suction and washed with ethyl acetate. There were obtained 1.65 g (85%) of rac-cis-3-cyclo-pentyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol hydro-chloride as pale rose crystals with m.p. 256°-258°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated, whereupon 100 ml of an aqueous NaHCO3 solution
  4. additiona small amount of 2N NaOH solution were added
  5. extractionthe mixture was extracted three times with CH2Cl2
  6. dry with materialthe extracts were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe brown crystals (1.7 g) were dissolved in 30 ml of ethanol
  10. filtrationThe separated crystals were filtered off under suction
  11. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-9bbf09182cc2465dad826666ab798eb4
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

Loading…