Ethanol → HCID 11719403, compound

HRID 604834Notes

Reaction equation

HRID 604834 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.[S:30](=[O:34])(=[O:33])([OH:32])[OH:31]>C(OCC)(=O)C>[S:30]([OH:34])([OH:33])(=[O:32])=[O: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 1118Sulfuric AcidHCID 11302685859217-52-0

Product 1

HCID 11719403HCID 11719403, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1-cyclopropylmethyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (310 mg, 0.874 mmol) were added ethyl alcohol (2.5 mL), 97% sulfuric acid (44.2 mg, 0.437 mmol) and ethyl acetate to form a thoroughly dissolved sate, followed by concentration under reduced pressure. To the obtained residual oil was added ethyl acetate to dissolve again, and the mixture was allowed to stand. The suspension containing precipitated crystals was concentrated to dryness under reduced pressure. A mixed solvent of diethyl ether and ethyl acetate was added to the suspension, and the solid was triturated by sonication. Precipitated crystals were collected by filtration, washed with diethyl ether, and aircured by aspiration. Drying under reduced pressure using a vacuum pump at room temperature gave 209 mg of the title compound as colorless crystals (crystal b).

Workup

  1. customto form a thoroughly dissolved sate
  2. concentrationfollowed by concentration under reduced pressure
  3. additionTo the obtained residual oil was added ethyl acetate
  4. dissolutionto dissolve again
  5. additionThe suspension containing
  6. customprecipitated crystals
  7. concentrationwas concentrated to dryness under reduced pressure
  8. additionA mixed solvent of diethyl ether and ethyl acetate was added to the suspension
  9. customthe solid was triturated by sonication
  10. customPrecipitated crystals
  11. filtrationwere collected by filtration
  12. washwashed with diethyl ether
  13. customDrying under reduced pressure
  14. customat room temperature

Sources & evidence

ORD record
ord-5fb95985c5ff419b9521c61098f380a3
Source dataset
uspto-grants-2011_03
Patent number
US07910734B2

Reaction notes

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