Potassium Iodide → HCID 20379985, compound

HRID 1658661Notes

Reaction equation

HRID 1658661 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21][CH2:22][CH2:23][CH2:24][C:25]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)=[O:26].C(=O)(O)[O-].[Na+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:21].[OH:8][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][C:25]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[O:26])[CH2:11][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 1235114-Chloro-1-(2-thienyl)butan-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 20379985HCID 20379985, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 53.5 g (0.2 moles) of α,α -diphenyl-4-piperidinemethanol, 41.5 g (0.22 mole) of 4-chloro-1-(2-thienyl)-1-butanone, 33.6 g (0.4 mole) of sodium bicarbonate and a small amount of potassium iodide in 1 liter of toluene was refluxed for 24 hours then filtered. The filtrate was cooled to room temperature, treated with charcoal, and filtered. The solvent was removed under vacuum and 500 ml of diethyl ether was added to dissolve the residue, followed by treatment with ethereal HCl. The resulting precipitate was recrystallized from methanolbutanone to give the desired product, M.P. 192.5°-193.5°C.

Workup

  1. filtrationthen filtered
  2. additiontreated with charcoal
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum and 500 ml of diethyl ether
  5. additionwas added
  6. dissolutionto dissolve the residue
  7. customThe resulting precipitate was recrystallized from methanolbutanone

Sources & evidence

ORD record
ord-cfbac79bf2cf4ca39a9c9ce27df78759
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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