Phosgene → HCID 23347353, compound

HRID 614367Notes

Reaction equation

HRID 614367 reaction equation
[C:1](Cl)(Cl)=[O:2].[OH:5][CH:6]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[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][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1.[OH-].[K+]>C1(C)C=CC=CC=1>[OH:5][CH:6]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[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][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:1]2=[O:2])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14797Potassium Hydroxide2×HCID 23347356HCID 23347356, compound

Product 1

HCID 23347353HCID 23347353, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

With vigorous stirring, 630 ml of a 20% solution of phosgene in toluene are added dropwise at a reaction temperature of 5° to 10° C in the course of 13/4 hours to an emulsion of 56 g of 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-[2-(4-chloroanilino)-ethylamino]-piperidine in 340 ml of toluene and 200 ml of a 3N potassium hydroxide solution. Thereafter 193 ml of a 6N aqueous potassium hydroxide solution are added dropwise at the same reaction temperature in the course of half an hour. The reaction mixture is further stirred for 1 hour at 5° to 10° C and for 20 hours at room temperature and then concentrated. The residue is made alkaline with a 2N aqueous sodium hydroxide solution and extracted with five 100 ml portions of methylene chloride. The extracts are dried over sodium sulphate and concentrated under reduced pressure. The residue is dissolved in methanol and boiled for 30 minutes with the addition of activated charcoal. The batch is filtered and the filtrate is concentrated under reduced pressure. The residue is treated with toluene and recrystallised from isopropanol to yield 1-{1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-piperidyl}-3-(4-chlorophenyl)-imidazolidin-2-one with a melting point of 136°-137° C.

Workup

  1. concentrationconcentrated
  2. extractionextracted with five 100 ml portions of methylene chloride
  3. dry with materialThe extracts are dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in methanol
  6. additionboiled for 30 minutes with the addition of activated charcoal
  7. filtrationThe batch is filtered
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. additionThe residue is treated with toluene
  10. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-8dd404ea543141eca0291d174ed5cd89
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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