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

HRID 1855984Notes

Reaction equation

HRID 1855984 reaction equation
[C:1](Cl)([Cl:3])=[O:2].[OH:5][CH:6]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1.[OH-].[Na+].[OH-].[K+]>C1(C)C=CC=CC=1>[ClH:3].[OH:5][CH:6]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH2:16][N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:1]2=[O:2])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 233473391-[2-Hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-(2-anilino-ethylamino)-piperidine

Product 1

HCID 233473351-{1-[2-Hydroxy-3-(2-methoxy-phenyloxy)-propyl]-4-piperidyl}-3-phenyl-imidazolidin-2-one-hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

With vigorous stirring, a solution of 117 ml of a 20% phosgene solution in toluene is added dropwise at a reaction temperature of 5° to 10° C. to an emulsion of 10 g of 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-(2-anilino-ethylamino)-piperidine in 60 ml of toluene and 37.5 ml of a 3 N aqueous sodium hydroxide solution over 11/4 hours. Thereafter 35.5 ml of a 6 N aqueous potassium hydroxide solution are added dropwise at the same reaction temperature in the course of half an hour. Stirring is continued for 30 minutes at 5° to 10° C. and for 20 hours at room temperature. The reaction mixture is filtered with suction and the crystalline residue is treated with toluene. Recrystallisation from isopropanol yields 1-{1-[2-hydroxy-3-(2-methoxy-phenyloxy)-propyl]-4-piperidyl}-3-phenyl-imidazolidin-2-one-hydrochloride in the form of white crystals with a melting point of 185°-187° C. The salt can be converted into the free compound for example by treatment with an aqueous sodium hydroxide solution.

Workup

  1. filtrationThe reaction mixture is filtered with suction
  2. additionthe crystalline residue is treated with toluene
  3. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-1a5597cf79b0419cb7debd04bd31b6a1
Source dataset
uspto-grants-1980_08
Patent number
US04217350

Reaction notes

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