Water → 4-[4-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]morpholin-3-one

HRID 1748617Notes

Reaction equation

HRID 1748617 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][OH:17])[CH2:10][CH:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:27][C:28](Cl)=[O:29].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:27][C:28]3=[O:29])[CH2:10][CH:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 866925612-[4-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]amino ethanol

Product 1

HCID 866925624-[4-(5-Bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]morpholin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-yl]aminoethanol (860 mg) and triethylamine (0.424 ml) in dichloromethane (10 ml) was added chloroacetic acid chloride (0.242 ml) under ice-cooling with stirring. The mixture was stirred at the same temperature for 1 hour, then water was added thereto, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was dissolved in isopropyl alcohol (10 ml), and hydroxide potassium (129 mg) was added thereto at room temperature with stirring. The mixture was stirred at the same temperature for 8 hours, and then to the reaction solution was added water, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (855 mg) as a white solid.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe obtained residue was dissolved in isopropyl alcohol (10 ml)
  7. additionhydroxide potassium (129 mg) was added
  8. stirringat room temperature with stirring
  9. stirringThe mixture was stirred at the same temperature for 8 hours
  10. additionto the reaction solution was added water
  11. extractionextracted with chloroform
  12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  13. customthe solvent was evaporated
  14. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0f0a9bb584a34a0f8cf34564d7803b38
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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