Ethyl Acetate → HCID 9820044, compound

HRID 1861661Notes

Reaction equation

HRID 1861661 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].Cl.[CH:23]1([CH2:29][CH2:30][NH:31][CH2:32][CH2:33][S:34][CH3:35])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(OCC)(=O)C>O1CCCC1>[CH:23]1([CH2:29][CH2:30][N:31]([CH2:32][CH2:33][S:34][CH3:35])[C:10]([NH:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:11])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 33944N-(2-Aminoethyl)piperidineHCID 682631,1'-CarbonyldiimidazoleHCID 22723059HCID 22723059, compound

Product 1

HCID 9820044HCID 9820044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-piperidyl) ethylamine (151 mg) in anhydrous tetrahydrofuran (5.9 ml), there was added 1,1′-carbonyl diimidazole (228 mg) in a nitrogen gas atmosphere and the resulting mixture was stirred at room temperature for 15 minutes. Then 2-cyclohexyl-N-[2-(methylthio) ethyl]-ethylamine hydrochloride (309 mg) was added to the foregoing mixture and the resulting mixture was refluxed with heating for 45 minutes. Ethyl acetate was added to the reaction solution with ice cooling, followed by washing the reaction solution with saturated aqueous solution of sodium hydrogen carbonate and then with saturated sodium chloride aqueous solution, drying over anhydrous sodium sulfate and concentration under reduced pressure. The resulting oily product was purified by the silica gel column chromatography to thus give the title compound (Compound 4-1).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperaturewith heating for 45 minutes
  3. washby washing the reaction solution with saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialwith saturated sodium chloride aqueous solution, drying over anhydrous sodium sulfate and concentration under reduced pressure
  5. customThe resulting oily product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-0760ec4632714e1e8491b2db9369a1e4
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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