3,4,5-Trimethoxyphenyl isothiocyanate → 4-(2-Chlorophenyl)-1-(3-[3,4,5-trimethoxyphenyl(thiocarbamoyl)oxy]propyl)piperazine, hydrochloride

HRID 5858노트

반응식

HRID 5858 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[S:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][OH:32])[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[ClH:16].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][CH2:31][O:32][C:14](=[S:15])[NH:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[CH2:27][CH2:28]1

참가 물질

4

반응물 2

HCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 2432883-(4-(2-Chlorophenyl)piperazin-1-yl)propan-1-ol

생성물 1

HCID 1317181664-(2-Chlorophenyl)-1-(3-[3,4,5-trimethoxyphenyl(thiocarbamoyl)oxy]propyl)piperazine, hydrochloride수율 42.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3,4,5-trimethoxyphenylisothiocyanate (2.0 mmol) (produced as in Example 22) and 3-[4-(2-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (40 ml) was refluxed for 16 h. The solvent was evaporated and the residue resuspended in ethyl acetate filtered and evaporated to dryness. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene/ethyl acetate (1:1). The product was taken up in ethanol, which was treated with hydrogen chloride in ether to give 220 mg of the title compound. M.p. 182°-183° C. MS (70 eV): m/z 479 (M+, 0.5%), 254 (47), 225 (82), 209 (100), 182 (29).

후처리

  1. temperaturewas refluxed for 16 h
  2. customThe solvent was evaporated
  3. filtrationfiltered
  4. customevaporated to dryness
  5. additionwhich was treated with hydrogen chloride in ether

출처 및 근거

ORD 기록
ord-7dae953e4f5249e8b8c29ff501f4aac0
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246935

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