Ethanol → HCID 11518342, compound

HRID 604835Notes

Reaction equation

HRID 604835 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH:17]3[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.C(O)C.[CH2:30]([S:32]([OH:35])(=[O:34])=[O:33])[CH3:31]>CCCCCCC>[CH2:30]([S:32]([OH:35])(=[O:34])=[O:33])[CH3:31].[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH:17]3[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([CH3:24])([CH3:23])[CH2:22]3)[CH2:9][CH2:10]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 11668Ethanesulfonic acidHCID 11302685859217-52-0

Product 1

HCID 11518342HCID 11518342, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Conditions

Temperature
78 °C

Procedure

To 1-cyclopropylmethyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (1.30 g, 3.67 mmol) were added ethyl alcohol (1.3 mL) and ethanesulfonic acid (412 mg, 3.74 mmol), followed by heating and stirring at an external temperature of 78° C. to form a thoroughly dissolved sate. To the mixture was slowly added heptane (7 mL) over 40 minutes, then was slowly added heptane (14 mL) over 35 minutes, and the external temperature was maintained at 78° C. for 20 minutes. The suspension containing precipitated crystals was stirred for 3 hours while slowly cooling the external temperature to 35° C. The mixture was stirred at room temperature for 30 minutes, then at an external temperature of 5° C. for 1 hour. Precipitated crystals were collected by suction filtration, and aircured by aspiration over 20 minutes with nitrogen gas. The crystals were dried under reduced pressure using a vacuum pump at room temperature for 4 hours, and hot-air dried at 50° C. for 4 hours and at 60° C. for 10 hours to give 1.64 g of the title compound as colorless crystals.

Workup

  1. temperatureby heating
  2. customto form a thoroughly dissolved sate
  3. customover 40 minutes
  4. customover 35 minutes
  5. temperaturethe external temperature was maintained at 78° C. for 20 minutes
  6. additionThe suspension containing
  7. customprecipitated crystals
  8. stirringwas stirred for 3 hours
  9. temperaturewhile slowly cooling the external temperature to 35° C
  10. stirringThe mixture was stirred at room temperature for 30 minutes
  11. customPrecipitated crystals
  12. filtrationwere collected by suction filtration
  13. waitaircured by aspiration over 20 minutes with nitrogen gas
  14. customThe crystals were dried under reduced pressure
  15. customat room temperature
  16. customfor 4 hours
  17. customhot-air dried at 50° C. for 4 hours and at 60° C. for 10 hours

Sources & evidence

ORD record
ord-50539ab45d0948f095fb918b7e808037
Source dataset
uspto-grants-2011_03
Patent number
US07910734B2

Reaction notes

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