Potassium Iodide → HCID 131717091, compound

HRID 1460226Notes

Reaction equation

HRID 1460226 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.C([O:25][C:26](=[O:41])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37]Cl)=[C:30]([O:39][CH3:40])[CH:29]=1)C.C(=O)([O-])[O-].[Na+:46].[Na+].[I-].[K+]>C(#N)C>[OH2:9].[Na+:46].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:37][CH2:36][CH2:35][O:34][C:31]3[CH:32]=[CH:33][C:28]([CH2:27][C:26]([O-:41])=[O:25])=[CH:29][C:30]=3[O:39][CH3:40])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 144071784-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester

Product 1

HCID 131717091HCID 131717091, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 2.9 g (0.01 mole) of 4-(3-chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 150 ml of acetonitrile was heated at reflux temperature for 20 hr. The mixture was concentrated under reduced pressure and the residue partitioned between benzene and water. The benzene layer was washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure to give the ethyl ester of the title compound as a gum. The gum was converted to the hydrochloride with ethereal hydrogen chloride to give a white solid. The solid could not be recrystallized so it was partitioned between methylene chloride and a 5% sodium hydroxide solution. An emulsion resulted which was let stand for 2 months while the layers separated. During this time a solid precipitated. The mixture was filtered. The filter cake was recrystallized from ethyl acetate to yield 0.7 g (13%) of the title compound as a fluffy, white solid, mp 102°-112° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between benzene and water
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-750e1de2fbbc4331b8064c00d963a31c
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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