5-Nonanone → HCID 178440921, compound

HRID 1355581Notes

Reaction equation

HRID 1355581 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C@H:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)[NH2:12])=[CH:2]1.[CH3:24][CH2:25][CH2:26][CH2:27][C:28](=O)[CH2:29][CH2:30][CH2:31][CH3:32]>C(O)CCC>[CH2:27]([C:28]1([CH2:29][CH2:30][CH2:31][CH3:32])[C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]=2[CH2:10][C@H:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)[NH:12]1)[CH2:26][CH2:25][CH3:24]

Participants

4

Reactant 2

HCID 104055-NonanoneHCID 178511813HCID 178511813, compound

Product 1

HCID 178440921HCID 178440921, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of (1R)-2-(1-benzothiophen-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine (1 g, 2.5 mmol) in n-butanol (20 ml) was added 5-nonanone (2.2 ml, 13 mmol) and the mixture refluxed overnight. The solvent was removed under reduced pressure. To the residue was added water (15 ml) followed by a 10% NaHCO3 solution until neutral pH and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with water (2×10 ml), dried over MgSO4, filtered. The solvent was evaporated under reduced pressure to afford an oil which was purified by column chromatography on silica gel using ethyl acetate/heptane 1:1 as eluent. After removing the solvent, diisopropyl ether was added to the residue. The resulting white precipitate was filtered off and washed with diisopropyl ether to afford 0.1 g of the title product. Melting point: 198-200° C.

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. additionTo the residue was added water (15 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. washThe combined organic extracts were washed with water (2×10 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customto afford an oil which
  10. customwas purified by column chromatography on silica gel
  11. customAfter removing the solvent, diisopropyl ether
  12. additionwas added to the residue
  13. filtrationThe resulting white precipitate was filtered off
  14. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-7c37b8fed9fb4e48a3d5b1f60a119043
Source dataset
uspto-grants-2003_07
Patent number
US06586445B1

Reaction notes

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