Potassium Iodide → 4'-Tert-butyl-4-[4-[alpha-(p-tolyl)benzylidene]piperidino]butyrophenone hydrochloride

HRID 1579329Notes

Reaction equation

HRID 1579329 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][Cl:36])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:36].[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][N:12]2[CH2:13][CH2:14][C:9](=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10][CH2:11]2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516893Potassium BicarbonateHCID 27236944'-tert-Butyl-4-chlorobutyrophenoneHCID 21568361alpha-Phenyl-alpha-(p-tolyl)-4-piperidinemethanol

Product 1

HCID 215683474'-Tert-butyl-4-[4-[alpha-(p-tolyl)benzylidene]piperidino]butyrophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 25.4 g (0.0905 mole) of α-phenyl-α-(p-tolyl)-4-piperidinemethanol, 26.2 g (0.11 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 22 g of potassium bicarbonate, 0.1 g of potassium iodide, 250 ml of toluene, and 40 ml of water is refluxed for 88 hours. Upon cooling to room temperature the toluene layer is separated, and the aqueous layer is extracted with toluene. The combined toluene extracts are dried over magnesium sulfate, filtered and the filtrate is treated with ethereal HCl. The resulting precipitate is filtered, triturated with ether, and recrystallized from butanone-ether to give 4'-tert-butyl-4-[4-[α-(p-tolyl)benzylidene]piperidino]butyrophenone hydrochloride, M.P. 187°-189°C.

Workup

  1. temperatureis refluxed for 88 hours
  2. customis separated
  3. extractionthe aqueous layer is extracted with toluene
  4. dry with materialThe combined toluene extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. additionthe filtrate is treated with ethereal HCl
  7. filtrationThe resulting precipitate is filtered
  8. customtriturated with ether
  9. customrecrystallized from butanone-ether

Sources & evidence

ORD record
ord-1d273f2d1eb44a9b86ee18af9ea6bf92
Source dataset
uspto-grants-1976_01
Patent number
US03931197

Reaction notes

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