Potassium Iodide → N-[2-(2-Hydroxyethoxy)-ethyl]-4,4-diphenylpiperidine

HRID 973708Notes

Reaction equation

HRID 973708 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([OH:25])[CH2:20][O:21][CH2:22][CH2:23]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.O1CCOCC1>[OH:25][CH2:19][CH2:20][O:21][CH2:22][CH2:23][N:10]1[CH2:9][CH2:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 28232394,4-Diphenylpiperidine

Product 1

HCID 19988807N-[2-(2-Hydroxyethoxy)-ethyl]-4,4-diphenylpiperidine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

82 g of 4,4-diphenylpiperidine, 50 g of diethylene glycol monochlorohydrin, 250 g of finely powdered potassium carbonate and 1 g of potassium iodide are heated at the boiling point under reflux, with vigorous stirring, in 1.2 l of a 1:1 mixture of dioxane and 1-butanol for 50 h. After cooling, the mixture is filtered and the filtrate is concentrated. The oily residue is taken up in ethyl acetate and the solution is filtered again. After the filtrate has been concentrated to constant weight (high vacuum), the title compound is obtained as a waxy viscous residue. Yield: 106 g. The hydrochloride is obtained with ethereal hydrochloric acid and is recrystallized from 2-propanol. M.p.: 120°-121° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. filtrationthe solution is filtered again
  5. concentrationAfter the filtrate has been concentrated to constant weight (high vacuum)

Sources & evidence

ORD record
ord-303b2f31c15545ed8a816c93fee59146
Source dataset
uspto-grants-1991_11
Patent number
US05064839

Reaction notes

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