Hydrochloric Acid → 1-{1-[2-Hydroxy-3-(2-methoxyphenoxy)-propyl]-4-piperidyl}-3-(4-methoxy-phenyl)-imidazolidin-2-one-hydrochloride

HRID 614368Notes

Reaction equation

HRID 614368 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:10]2=[O:20])=[CH:5][CH:4]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH2:30][CH:31]1[O:33][CH2:32]1.[ClH:34]>C(O)(C)C>[ClH:34].[OH:33][CH:31]([CH2:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[O:22][CH3:21])[CH2:32][N:17]1[CH2:18][CH2:19][CH:14]([N:11]2[CH2:12][CH2:13][N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:10]2=[O:20])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 98357((o-Methoxyphenoxy)methyl)oxiraneHCID 233473361-(4-Methoxyphenyl)3-(4-piperidyl)-2-imidazolidinone

Product 1

HCID 233473501-{1-[2-Hydroxy-3-(2-methoxyphenoxy)-propyl]-4-piperidyl}-3-(4-methoxy-phenyl)-imidazolidin-2-one-hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 17.9 g of 1-[4-methoxy-phenyl)-3-(4-piperidyl)-2-imidazolidinone and 11.7 g of 1-(2-methoxyphenyloxy)-2,3-epoxypropane in 200 ml of isopropyl alcohol is refluxed for 6 hours. The mixture is thereafter acidified with 5N methanolic hydrochloric acid and concentrated under reduced pressure. The residue is freed from moisture still adhering to it by treatment with toluene. Recrystallisation of the residue from methanol with the addition of activated charcoal yields the 1-{1-[2-hydroxy-3-(2-methoxyphenoxy)-propyl]-4-piperidyl}-3-(4-methoxy-phenyl)-imidazolidin-2-one-hydrochloride as a white crystalline substance with a melting point of 214°-215° C.

Workup

  1. temperatureis refluxed for 6 hours
  2. concentrationconcentrated under reduced pressure
  3. customRecrystallisation of the residue from methanol
  4. additionwith the addition of activated charcoal

Sources & evidence

ORD record
ord-b2da3d3a4b7b4524a8e73d1382bc0e3e
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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