Hydrochloric Acid → 4-(1H-Indol-3-YL)cyclohexanone

HRID 893328Notes

Reaction equation

HRID 893328 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1.Cl>CC(C)=O>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)=[CH:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 108487533-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indole

Product 1

HCID 108462644-(1H-Indol-3-YL)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(1H-3-indolyl)cyclohexanone ethylene ketal (66.4 g, 0.258 mol) is dissolved in 350 mL of acetone and 350 mL of 10% hydrochloric acid solution and allowed to stir at room temperature for 6 hours. The acetone is removed under reduced pressure and the mixture is made basic with concentrated ammonium hydroxide. The mixture is extracted with chloroform. The organic fraction is dried with sodium sulfate and volatiles are removed under reduced pressure. The resulting solid is taken up in hot ethyl acetate and upon cooling and filtration a crystalline solid is obtained (36.89 g).

Workup

  1. customThe acetone is removed under reduced pressure
  2. extractionThe mixture is extracted with chloroform
  3. dry with materialThe organic fraction is dried with sodium sulfate and volatiles
  4. customare removed under reduced pressure
  5. temperatureupon cooling
  6. filtrationfiltration a crystalline solid
  7. customis obtained (36.89 g)

Sources & evidence

ORD record
ord-e11db9076f1d46db8623330ec64d75cd
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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