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

HRID 1579326Notes

Reaction equation

HRID 1579326 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)[OH:8])[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][CH:9]([C:7]([OH:8])([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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 215683424'-Tert-butyl-4-[4-[alpha-hydroxy-alpha-(p-tolyl)benzyl]-piperidino]butyrophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 29.0 g (0.1 mole) of α-phenyl-α-(p-tolyl)-4-piperidinemethanol, 32 g (0.12 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 20 g of potassium bicarbonate, 0.1 g of potassium iodide, 300 ml of toluene and 50 ml of water is stirred on a steam bath for 88 hours. Upon cooling to room temperature the toluene layer is separated, and the aqueous layer is extracted with toluene. The combined toluene fractions are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to an oil. The oily residue is dissolved in dry ether and filtered. The filtrate is treated with ethereal HCl, and the resulting precipitate is collected and recrystallized from methanol-butanone to give 4'-tert-butyl-4-[4-[α-hydroxy-α-(p-tolyl)benzyl]-piperidino]butyrophenone hydrochloride, M.P. 194°-196.5°C.

Workup

  1. customis separated
  2. extractionthe aqueous layer is extracted with toluene
  3. washThe combined toluene fractions are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThe oily residue is dissolved in dry ether
  8. filtrationfiltered
  9. additionThe filtrate is treated with ethereal HCl
  10. customthe resulting precipitate is collected
  11. customrecrystallized from methanol-butanone

Sources & evidence

ORD record
ord-70a8fd652fee4eeda76ee9724cbc3fc0
Source dataset
uspto-grants-1976_01
Patent number
US03931197

Reaction notes

Loading…