Potassium Iodide → HCID 20379982, compound

HRID 1658670Notes

Reaction equation

HRID 1658670 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C: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[CH2:21][CH2:22][CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:25].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:24](=[O:25])[CH2:23][CH2:22][CH2:21][N:11]2[CH2:10][CH2:9][C:8](=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13][CH2:12]2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 516893Potassium BicarbonateHCID 27625334-(Diphenylmethylene)piperidine

Product 1

HCID 20379982HCID 20379982, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 99.9 g (0.4 mole) of 4-diphenylmethylenepiperidine, 88 g (0.44 mole) of 4-chloro-4'-fluorobutyrophenone, 64.0 g (0.64 mole) of potassium bicarbonate and a small amount of potassium iodide in 1500 ml of toluene was refluxed for 5 days. The reaction mixture was filtered, and the filtrate was concentrated at reduced pressure leaving a residue which was dissolved in about 800 ml of ethyl acetate. This solution was concentrated to about 500 ml and allowed to stand for one day. The resulting precipitate was recrystallized from methanolethyl acetate, made basic with sodium hydroxide solution, water washed, and the product recrystallized from 75°-90° petroleum ether to give the title compound, M.P. 111°-114° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated at reduced pressure
  3. customleaving a residue which
  4. concentrationThis solution was concentrated to about 500 ml
  5. customThe resulting precipitate was recrystallized from methanolethyl acetate
  6. washwashed
  7. customthe product recrystallized from 75°-90° petroleum ether

Sources & evidence

ORD record
ord-9035fe5031dd4796aecb340fc9727f1d
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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