5-Nonanone → HCID 9803492, compound

HRID 1355584Notes

Reaction equation

HRID 1355584 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[NH2:13])=[CH:3]1.[CH3:25][CH2:26][CH2:27][CH2:28][C:29](=O)[CH2:30][CH2:31][CH2:32][CH3:33]>C(O)CCC>[CH2:28]([C:29]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:3]2[NH:2][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH2:11][C@H:12]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[NH:13]1)[CH2:27][CH2:26][CH3:25]

Participants

4

Reactant 2

HCID 104055-NonanoneHCID 69876321HCID 69876321, compound

Product 1

HCID 9803492HCID 9803492, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1,3-thiazol-2-yl)-1-ethanamine hydrochloride (210 mg, 0.59 mmol) in n-butanol (15 ml) was added 0.45 ml (2.5 mmol) of 5-nonanone. The mixture was heated under reflux for about two hours and then 5 ml of n-butanol was removed by Dean-Stark. Reflux was continued for about 3 hours. The mixture was concentrated under reduced pressure and the residue partitioned between 15 ml ethyl acetate and 15 ml 10% NaHCO3 solution. After decantation the organic layer was washed with water and dried over MgSO4. Evaporation of the solvent afforded a residue which was purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate 97:3). The pure fractions were collected and concentrated. The residue was dissolved in diethyl ether, and 1N HCl in ethyl acetate was added. The hydrochloride was collected by filtration and washed with diethyl ether to give 85 mg of the title product as an orange powder. Melting point: 134-136° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for about two hours
  3. custom5 ml of n-butanol was removed by Dean-Stark
  4. temperatureReflux
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue partitioned between 15 ml ethyl acetate and 15 ml 10% NaHCO3 solution
  7. washAfter decantation the organic layer was washed with water
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent
  10. customafforded a residue which
  11. customwas purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate 97:3)
  12. customThe pure fractions were collected
  13. concentrationconcentrated
  14. dissolutionThe residue was dissolved in diethyl ether
  15. addition1N HCl in ethyl acetate was added
  16. filtrationThe hydrochloride was collected by filtration
  17. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f781c659604f4d9d84b6c97058ccc84f
Source dataset
uspto-grants-2003_07
Patent number
US06586445B1

Reaction notes

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