Potassium Iodide → HCID 20356972, compound

HRID 2083669Notes

Reaction equation

HRID 2083669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[I-].[K+].[OH-].[K+].[C:19]1([C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH2:28][CH2:29]Br)[C:26]#[N:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)C.O>[ClH:1].[C:31]1([C:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([CH2:28][CH2:29][N:11]2[CH2:10][CH2:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([OH:14])[CH2:13][CH2:12]2)[C:26]#[N:27])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 965754-Bromo-2,2-diphenylbutyronitrile

Product 1

HCID 20356972HCID 20356972, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 4.87 parts of 4-(4-chlorophenyl)piperidin-4-ol and 1.91 parts of potassium iodide in 25 parts of deionized water is heated and stirred under a nitrogen atmosphere. When the temperature reaches about 30° - 35° C., 1.65 parts of potassium hydroxide is added. The heating is continued to a temperature of about 45° - 55° C., at which time 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile is added. The temperature is raised to reflux and maintained thereat for 4.5 hours. After cooling to about 30° C., 29 parts of ethyl ether is added with stirring. The ether and water layers are separated and the water layer re-extracted with 7 parts of ethyl ether. The ether extracts are combined and washed twice with 12 part portions of dilute acetic acid. A solution of hydrochloric acid in isopropanol is added to form a precipitate which is filtered, washed with ethyl ether, and air-dried. The dried soild, 2,2-diphenyl-4-[4-(4-chlorophenyl)-4-hydroxypiperidino]butyronitrile hydrochloride is obtained in 90.7% yield. The solid is dissolved in dilute ammonium hydroxide and extracted with ethyl ether. The solvent is removed from the ether extract under reduced pressure to afford as a white glass, 2,2-diphenyl-4-[4-(4-chlorophenyl)-4-hydroxypiperidino]-butyronitrile, represented by the following structural formula. ##STR15##

Workup

  1. customreaches about 30° - 35° C.
  2. additionis added
  3. temperatureThe temperature is raised
  4. temperatureto reflux
  5. temperaturemaintained
  6. stirringwith stirring
  7. customThe ether and water layers are separated
  8. extractionthe water layer re-extracted with 7 parts of ethyl ether
  9. washwashed twice with 12 part portions of dilute acetic acid
  10. additionA solution of hydrochloric acid in isopropanol is added
  11. customto form a precipitate which
  12. filtrationis filtered
  13. washwashed with ethyl ether
  14. customair-dried

Sources & evidence

ORD record
ord-a1b600eb361a4f3d82630a2eac8a62f7
Source dataset
uspto-grants-1978_04
Patent number
US04086234

Reaction notes

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