Potassium Iodide → HCID 70373348, compound

HRID 1709904Notes

Reaction equation

HRID 1709904 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:37])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35]Cl)=[CH:28][CH:27]=1.[C:38](=[O:41])([O-:40])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[C:25]([OH:37])(=[O:24])/[CH:26]=[CH:27]/[C:38]([OH:40])=[O:41].[CH3:23][O:24][C:25](=[O:37])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][N:13]2[CH2:12][CH2:11][CH:10]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:9])[CH2:15][CH2:14]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 70373348HCID 70373348, compoundYield 136.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.1 g (0.03 mole) of α, α-bis(p-fluorophenyl)-4-piperidinemethanol, 6.7 g (0.03 mole) of 4-(3-chloropropoxy)benzoic acid methyl ester, 10.6 g (0.1 mole) of anhydrous sodium carbonate and 0.6 g of potassium iodide in 125 ml of dimethylformamide was heated in a steambath for 25 hr. The reaction mixture was poured into 1.5 liters of ice-water. The resulting solid was collected by filtration, washed with water and dried. The solid was converted to the fumaric acid salt to yield 12.5 g (68%) of title compound as a white solid, mp 140°-174° C. with decomposition.

Workup

  1. temperaturewas heated in a steambath for 25 hr
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-27f831a404e346c998ffeca0802d876d
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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