3-(4-(2-Chlorophenyl)piperazin-1-yl)propan-1-ol → 4-(2-Chlorophenyl)-1-[3-(3,4-ethylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochloride

HRID 5852

Reaktionsgleichung

Reaktionsgleichung von HRID 5852
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([N:11]=[C:12]=[O:13])=[CH:4][C:3]=2[O:2]1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][OH:30])[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[ClH:14].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][CH2:29][O:30][C:12](=[O:13])[NH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:10][CH2:1][O:2][C:3]=3[CH:4]=2)[CH2:25][CH2:26]1

Komponenten

4

Edukt 2

HCID 2432883-(4-(2-Chlorophenyl)piperazin-1-yl)propan-1-olHCID 27761726-Isocyanato-2,3-dihydro-1,4-benzodioxine

Produkt 1

HCID 1317181634-(2-Chlorophenyl)-1-[3-(3,4-ethylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochlorideAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3,4-ethylenedioxyphenylisocyanate (2.0 mmol) (produced as in Example 16) and 3-[4-(2-chlorophenyl)-1piperazinyl]propanol (500 mg; 2.0 mmol) in toluene (10 ml) was refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:5). The product was taken up in ethyl acetate which was treated with hydrogen chloride in ether. Recrystallization from methanol/ether afforded 330 mg of the title compound. M.p. 205°-206° C. MS (70 eV): m/z 431 (14%, M+), 209 (100), 177 (70), 121 (44), 93 (38), 70 (56).

Aufarbeitung

  1. temperaturewas refluxed for 16 h
  2. concentrationThe reaction mixture was then concentrated
  3. additionwas treated with hydrogen chloride in ether
  4. customRecrystallization from methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-a42846c208cf4c61a676ead8d617e1cf
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246935

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