Hydrochloric Acid → HCID 131718484, compound

HRID 1109146Notes

Reaction equation

HRID 1109146 reaction equation
C[O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[ClH:24]>Br>[ClH:24].[ClH:24].[N:18]1([CH2:17][CH2:16][N:11]2[C@@H:12]3[C@@H:8]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([OH:2])[C:15]=4[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131718483HCID 131718483, compound

Product 1

HCID 131718484HCID 131718484, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3.8 g (0.0121 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-piperidinoethyl)-1H-benzo[e]indole were dissolved in 0.351 of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was concentrated and the residue was taken up in CH2Cl2 and extracted with a mixture of 100 ml of saturated NaHCO3 solution and 20 ml of 2N NaOH solution. The extracts were dried with MgSO4, filtered and concentrated. The foam (3.8 g) remaining as the residue was dissolved in 50 ml of ethanol. The mixture was filtered, 4.8 ml (27.84 mmol) 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 4.3 g (95%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(2 -piperidinoethyl)-1H-benzo[e]indol-6-ol dihydrochloride as white crystals with m.p. 265°-267°.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe mixture was concentrated
  3. extractionextracted with a mixture of 100 ml of saturated NaHCO3 solution and 20 ml of 2N NaOH solution
  4. dry with materialThe extracts were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionwas dissolved in 50 ml of ethanol
  8. filtrationThe mixture was filtered
  9. filtrationThe separated crystals were filtered off under suction
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d43b888aaf6c4f79b87b4162409296a1
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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