Potassium Carbonate → HCID 23441037, compound

HRID 2119344Notes

Reaction equation

HRID 2119344 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[CH2:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:20][CH2:21][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2283651-Benzyl-1,4-diazepaneHCID 222382923,3-Diphenylpropyl methanesulfonate

Product 1

HCID 23441037HCID 23441037, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The resulting benzyihomopiperazine was dissolved in 3 mL of ethanol, to which were added 296 mg of 3,3-diphenylpropyl methanesulfonate and 136 mg of potassium carbonate. The mixture was stirred at 70° C. for 15 hours and it was cooled to room temperature and the solvent was removed under reduced pressure. 20 mL of aqueous 2N sodium hydroxide was added and the solution was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined and washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate) to obtain 135 mg of the titled compound. This was treated with a hydrogen chloride solution in ether followed by removing the solvent under reduced pressure and drying to give the hydrochloride salt of the titled compound.

Workup

  1. temperatureit was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. addition20 mL of aqueous 2N sodium hydroxide was added
  4. extractionthe solution was extracted with 20 mL×2 of ethyl acetate
  5. washwashed with 20 mL of saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-22ffe9027fea4584bd2783c8ece1dba3
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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