Potassium Hydroxide → HCID 90026369, compound

HRID 1484427Notes

Reaction equation

HRID 1484427 reaction equation
C([N:6]1[CH2:27][CH2:26][C:9]2[N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)(OCC)=O.[OH-].[K+]>C(O)C>[Br:17][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9]3[CH2:26][CH2:27][NH:6][CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 90024195HCID 90024195, compound

Product 1

HCID 90026369HCID 90026369, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-carbethoxy-8-bromo-5-n-octyl-1,2,3,4-tetrahydropyrido[4,3-b]indole (4b) in ethanol was added the aqueous solution of potassium hydroxide. The mixture was refluxed for 16 h. The reaction mixture was concentrated to remove ethanol and extracted with DCM for three times (15 mL×3). The DCM layer was washed with brine, dried with Na2SO4, filtered and concentrated to give brow residue. This residue was purified by silica gel column chromatography to give yellow oil. Yield: 74.5%.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. customto remove ethanol
  4. extractionextracted with DCM for three times (15 mL×3)
  5. washThe DCM layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give brow residue
  10. customThis residue was purified by silica gel column chromatography
  11. customto give yellow oil

Sources & evidence

ORD record
ord-c4b1b074e46e4432aaffed606d39415b
Source dataset
uspto-grants-2016_08
Patent number
US09422238B2

Reaction notes

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