Potassium Hydroxide → HCID 23312290, compound

HRID 745819Notes

Reaction equation

HRID 745819 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[O:16][C:15]3[CH:17]=[CH:18][C:19]4[C:24]([C:14]=3[CH:13]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)CO>[CH:13]1[C:14]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][C:15]=2[O:16][C:12]=1[CH:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54207843HCID 54207843, compound

Product 1

HCID 23312290HCID 23312290, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

7.8 g of 4-(naphtho[2,1-b]furan-2-yl)-1-piperidinecarboxylic acid ethyl ester is dissolved in 60 ml of ethylene glycol. After the addition of 40 ml of a 50% aqueous potassium hydroxide solution, the formed cloudy solution is heated, with vigorous stirring, for 15 hours at 160°. The reaction solution is thereupon cooled to 20° and extracted twice with 500 ml of ethyl acetate. The organic phases are washed five times with 1 liter of water each time, dried over sodium sulphate, filtered, and concentrated by evaporation. The residue is dissolved in 400 ml of 2N hydrochloric acid, and the acid solution extracted with toluene. The aqueous solution is then adjusted by addition of 10% sodium hydroxide solution to have a pH value of 12, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered, and concentrated by evaporation to obtain crude 4-(naphtho[2,1-b]furan-2-yl)-piperidine. The hydrochloride is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 225°.

Workup

  1. temperaturethe formed cloudy solution is heated, with vigorous stirring, for 15 hours at 160°
  2. temperatureThe reaction solution is thereupon cooled to 20°
  3. extractionextracted twice with 500 ml of ethyl acetate
  4. washThe organic phases are washed five times with 1 liter of water each time
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. dissolutionThe residue is dissolved in 400 ml of 2N hydrochloric acid
  9. extractionthe acid solution extracted with toluene
  10. additionThe aqueous solution is then adjusted by addition of 10% sodium hydroxide solution
  11. extractionextracted with 1 liter of chloroform
  12. dry with materialThe chloroform solution is dried with sodium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8d57b6a87cb1413c827ac21b1eb77af4
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

Loading…