HCID 19778092, compound → HCID 9796680, compound

HRID 2082321Notes

Reaction equation

HRID 2082321 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([N:10]1[CH:23]=[CH:22][C:13]3[N:14]([CH3:21])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[C:11]1=[O:24])[CH2:3]2>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([N:10]1[CH2:23][CH2:22][C:13]3[N:14]([CH3:21])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[C:11]1=[O:24])[CH2:3]2

Participants

4

Reactant 1

HCID 19778092HCID 19778092, compound

Product 1

HCID 9796680HCID 9796680, compoundYield 164.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

(RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2-dihydro-5-methyl-1-oxopyrido[4,3-b]indole hydrochloride (0.3 g, 0.98 mmol), from Example 3, in acetic acid (5 ml, containing 3 drops of 70% perchloric acid) was reduced with 20% palladium hydroxide on carbon (0.1 g) at 80° C. and 350 kPa for 20 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in water (10 ml), basified with ammonium hydroxide solution and extracted with ethyl acetate. The ethyl acetate was dried over anhydrous potassium carbonate, filtered and evaporated. The residue was purified by column chromatography (10% methanol in dichloromethane +1% ammonium hydroxide; silica; Rf. 0.3) to afford 0.5 g (16% yield) of (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydro-5-methyl-1-oxopyrido[4,3-b]indole.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (10 ml)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate was dried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (10% methanol in dichloromethane +1% ammonium hydroxide; silica; Rf. 0.3)

Sources & evidence

ORD record
ord-562b64e839a142c8b482c8492a4487f5
Source dataset
uspto-grants-1993_02
Patent number
US05189041

Reaction notes

Loading…