1-Phenylpiperazine → 3-[4-(4-Chlorophenyl)-2-(4-phenyl-l-piperazinyl)-5-oxazolyl]propionic acid

HRID 350743노트

반응식

HRID 350743 반응식
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

생성물 1

HCID 210886453-[4-(4-Chlorophenyl)-2-(4-phenyl-l-piperazinyl)-5-oxazolyl]propionic acid수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (1.0 g), 1-phenylpiperazine (2.27 g), potassium carbonate (2.42 g) and N,N-dimethylformamide (20 mL) was stirred at 100° C. for 3 hrs. The reaction mixture was poured into aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography and 3-[4-(4-chlorophenyl)-2-(4-phenyl-l-piperazinyl)-5-oxazolyl]propionic acid (0.76 g, yield 53%) was obtained as a powder from a fraction eluted with ethyl acetate-chloroform-methanol (10:10:1, volume ratio). Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 177–178° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c70f9d88ad9b4b9e981f5d7c8d433fa1
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183276B2

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