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

HRID 5850

반응식

HRID 5850 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N:10]=[C:11]=[O:12])=[CH:4][C:3]=2[O:2]1.[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1>C1(C)C=CC=CC=1>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][O:29][C:11](=[O:12])[NH:10][C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[CH2:24][CH2:25]2)[CH:17]=[CH:18][CH:19]=1

참가 물질

4

반응물 2

HCID 2574073-(4-(3-Chlorophenyl)piperazin-1-yl)propan-1-olHCID 52232135-Isocyanato-1,3-dioxaindane

생성물 1

HCID 1317181624-(3-Chlorophenyl)-1-[3-(3,4-methylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochloride수율 187.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3,4-methylenedioxyphenylisocyanate (330 mg; 2.0 mmol) (produced as in Example 13) and 3-[4-(3-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 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 (1:3). The product was taken up in ethanol which was treated with hydrogen chloride in ether. Recrystallization from methanol/ether afforded 850 mg of the title compound M.p. 182°-184° C. MS (70 eV): m/z 417 (42%, M+), 254 (24), 209 (100), 194 (7), 163 (70), 136 (37), 70 (51).

후처리

  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

출처 및 근거

ORD 기록
ord-b553bc63e457446caa9f52fa9caba4ba
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246935

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