5-Nonanone → HCID 9844775, compound

HRID 1355578Notes

Reaction equation

HRID 1355578 reaction equation
[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([C@H:9]([NH2:20])[CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[O:6][C:7]=1[CH3:8].[CH3:21][CH2:22][CH2:23][CH2:24][C:25](=O)[CH2:26][CH2:27][CH2:28][CH3:29]>C(O)(C)C>[ClH:1].[CH2:24]([C:25]1([CH2:26][CH2:27][CH2:28][CH3:29])[C:12]2[NH:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]=2[CH2:10][C@H:9]([C:5]2[O:6][C:7]([CH3:8])=[C:3]([CH3:2])[N:4]=2)[NH:20]1)[CH2:23][CH2:22][CH3:21]

Participants

4

Reactant 2

HCID 104055-NonanoneHCID 69876357HCID 69876357, compound

Product 1

HCID 9844775HCID 9844775, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (1R)-1-(4,5-dimethyl-1,3-oxazol-2-yl)-2-(1H-indol-3-yl)-1-ethanamine hydrochloride (1.2 g, 3.6 mmol) in isopropanol (20 ml) was added 5-nonanone (3.1 ml, 20 mmol) and the mixture was refluxed for about 24 hours. The solvent was evaporated under reduced pressure. To the residue was added water (20 ml) followed by NaHCO3 (10%) solution until neutral pH, followed by ethyl acetate (3×15 ml). After decantation and extraction the combined organic extracts were washed with water (20 ml) and dried over MgSO4. The solvent was evaporated under reduced pressure to afford an oil which was purified by column chromatography on silica gel using ethyl acetate/heptane 7:3 as eluent. The resulting oil was dissolved in ethyl acetate (15 ml) and a solution of HCl in ethyl acetate (1N) was slowly added at about 20° C. to give a precipitate. The suspension was stirred a few minutes and the precipitate collected by filtration, washed with diethyl ether, and dried to afford 0.14 g the desired product as the hydrochloride salt. Melting point: 128-134° C.

Workup

  1. temperaturethe mixture was refluxed for about 24 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionTo the residue was added water (20 ml)
  4. extractionAfter decantation and extraction the combined organic extracts
  5. washwere washed with water (20 ml)
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated under reduced pressure
  8. customto afford an oil which
  9. customwas purified by column chromatography on silica gel
  10. dissolutionThe resulting oil was dissolved in ethyl acetate (15 ml)
  11. additiona solution of HCl in ethyl acetate (1N) was slowly added at about 20° C.
  12. customto give a precipitate
  13. filtrationthe precipitate collected by filtration
  14. washwashed with diethyl ether
  15. customdried

Sources & evidence

ORD record
ord-0188ef1d8d684e1084ea89d7d5d9937b
Source dataset
uspto-grants-2003_07
Patent number
US06586445B1

Reaction notes

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