Potassium Iodide → HCID 21528617, compound

HRID 1658667Notes

Reaction equation

HRID 1658667 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:20].[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 882784-BenzhydrylpiperidineHCID 2535334-Chlorobutyrophenone

Product 1

HCID 21528617HCID 21528617, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 175.5 g (0.7 mole) of 4-diphenylmethylpiperidine, 63.6 g (0.35 mole) of 4-chlorobutyrophenone, 600 ml of toluene, and a small amount of potassium iodide was refluxed for three days then allowed to stand at room temperature one day. The solvent was removed at reduced pressure, and one liter of dry ether was added after which the mixture was filtered. The filtrate was concentrated, and the residue was dissolved in 75°-90° petroleum ether treated with charcoal and filtered. The filtrate was cooled to room temperature and the resulting precipitate was filtered off, and dissolved in ether then treated with ethereal HCl. A precipitate formed which was recrystallized from methanol-butanone to give the desired product, M.P. 163.5°-164.5° C.

Workup

  1. customThe solvent was removed at reduced pressure, and one liter of dry ether
  2. additionwas added after which the mixture
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in 75°-90° petroleum ether
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. filtrationthe resulting precipitate was filtered off
  9. dissolutiondissolved in ether
  10. additionthen treated with ethereal HCl
  11. customA precipitate formed which
  12. customwas recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-b8231580c6d148d1987c12f6ccfdafef
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

Loading…