Potassium Carbonate → HCID 19418950, compound

HRID 864478Notes

Reaction equation

HRID 864478 reaction equation
C(=O)([O-])[O-].[K+].[K+].S(O[CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:15]1=[O:23])(C)(=O)=O.[CH2:24]1[C:29]2[NH:30][C:31]3[C:36]([C:28]=2[CH2:27][CH2:26][NH:25]1)=[CH:35][CH:34]=[CH:33][CH:32]=3>C(#N)C>[CH2:24]1[C:29]2[NH:30][C:31]3[C:36]([C:28]=2[CH2:27][CH2:26][N:25]1[CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:15]1=[O:23])=[CH:35][CH:34]=[CH:33][CH:32]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107838Tetrahydro-beta-carbolineHCID 19418949HCID 19418949, compound

Product 1

HCID 19418950HCID 19418950, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.828 g, 6 mmol), 3-(2-mesyloxyethyl)benzoxazolin-2-one (1.494 g, 5.814 mmol) and 1,2,3,4-tetrahydropyrido[3,4-b]indole (1 g, 5.814 mmol) in acetonitrile (30 ml) were heated under reflux under nitrogen for 16 hours. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (80 ml) and water (30 ml). The water was separated and hydrochloric acid (0.5M, 40 ml) was added. The resultant white precipitate was collected by filtration and suspended in sodium hyroxide (2M, 60 ml) and washed with chloroform (3×50 ml). The combined chloroform extracts were washed with water (30 ml), dried (MgSO4), and the solvent filtered and evaporated in vacuo. The residue was treated with diethyl ether/ethyl acetate (3:1, 40 ml) and a fine flocculent precipitate resulted. The resultant filtrate was evaporated in vacuo and the residue chromatographed on silica (ethyl acetate 40-60 petrol 3:2) to give the title product, melting point 135°-137° C.

Workup

  1. temperatureunder reflux under nitrogen for 16 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between ethyl acetate (80 ml) and water (30 ml)
  4. customThe water was separated
  5. additionhydrochloric acid (0.5M, 40 ml) was added
  6. filtrationThe resultant white precipitate was collected by filtration
  7. washwashed with chloroform (3×50 ml)
  8. washThe combined chloroform extracts were washed with water (30 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationthe solvent filtered
  11. customevaporated in vacuo
  12. additionThe residue was treated with diethyl ether/ethyl acetate (3:1, 40 ml)
  13. customa fine flocculent precipitate resulted
  14. customThe resultant filtrate was evaporated in vacuo
  15. customthe residue chromatographed on silica (ethyl acetate 40-60 petrol 3:2)

Sources & evidence

ORD record
ord-6ca13a82741b48c386f5fe130cbbcee7
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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