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

HRID 614361노트

반응식

HRID 614361 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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 3N aqueous sodium hydroxide solution over 11/4 hours. Thereafter 35.5 ml of a 6N 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.

후처리

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

출처 및 근거

ORD 기록
ord-f8441a4fbb5a4318be132ef77417aa09
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04144344

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