4-(9-Xanthenylidene)piperidine → 4-[4-(9-Xanthenylidene)piperidino]-2-butanone

HRID 616218Notes

Reaction equation

HRID 616218 reaction equation
[CH:1]1[C:14]2[C:13](=[C:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>[OH-].C(C([NH3+])(CC1C=CC=CC=1)CC1C=CC=CC=1)C1C=CC=CC=1.C(O)C.CC(C=C)=O>[CH:11]1[C:12]2[C:13](=[C:15]3[CH2:20][CH2:19][N:18]([CH2:3][CH2:4][C:5](=[O:6])[CH3:14])[CH2:17][CH2:16]3)[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[O:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 157805164-(9-Xanthenylidene)piperidine

Product 1

HCID 203715494-[4-(9-Xanthenylidene)piperidino]-2-butanone

Reagents, catalysts & solvents 3

HCID 21829752Tribenzylmethyl ammonium hydroxideCatalystHCID 702EthanolSolventHCID 6570Methyl vinyl ketoneSolvent

Procedure

One drop of tribenzylmethyl ammonium hydroxide is added to a solution of 7 g of 4-(9-xanthenylidene)-piperidine in 70 cc of ethanol, 4.38 cc of methylvinylketone are then added dropwise, and stirring is effected at 50° for 4 hours. The reaction mixture is then concentrated by evaporation in a vacuum, the residue is dissolved in chloroform, extraction is effected with water, and after drying over magnesium sulphate, concentration is effected by evaporation. The partially crystalline residue is triturated with ether/petroleum ether 1:1 and recrystallized from ethanol. M.P. of the title compound 111°-112°.

Workup

  1. additionare then added dropwise
  2. concentrationThe reaction mixture is then concentrated by evaporation in a vacuum
  3. dissolutionthe residue is dissolved in chloroform
  4. extractionextraction
  5. dry with materialafter drying over magnesium sulphate, concentration
  6. customis effected by evaporation
  7. customThe partially crystalline residue is triturated with ether/petroleum ether 1:1
  8. customrecrystallized from ethanol
  9. customM.P. of the title compound 111°-112°

Sources & evidence

ORD record
ord-20235b3223a44cbda69c7b47faca4260
Source dataset
uspto-grants-1978_02
Patent number
US04072756

Reaction notes

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