Sodium Hydroxide → HCID 131718480, compound

HRID 1109218Notes

Reaction equation

HRID 1109218 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][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>Br>[N:19]1([CH2:18][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)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131718479HCID 131718479, compound

Product 1

HCID 131718480HCID 131718480, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3.75 g (0.01135 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-morpholin-4-yl-propyl)-1H-benzo[e]indole were dissolved in 0.13 l of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 46.3 g (1.16 mol) of NaOH. After the addition of solid NaHCO3 the mixture was extracted three times with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. By chromatography over silica gel with methanol there were obtained 3.20 g (89%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-morpholin-4-yl-propyl)-1H-benzo[e]indol-6-ol.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionwas extracted three times with CH2Cl2
  3. washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac3dc2db9d844954ad0a119af52c38e3
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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