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

HRID 5857

反応式

HRID 5857 の反応式
[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:18]=[C:19]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][OH:32])[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[ClH:16].[Cl:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][CH2:31][O:32][C:14](=[S:15])[NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH2:27][CH2:28]2)[CH:20]=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 2574073-(4-(3-Chlorophenyl)piperazin-1-yl)propan-1-ol

生成物 1

HCID 1317181654-(3-Chlorophenyl)-1-(3-[3,4,5-trimethoxyphenyl(thiocarbamoyl)oxy]propyl)piperazine, hydrochloride収率 38.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3,4,5-trimethoxyphenylisothiocyanate (2.0 mmol) (produced as in Example 22) and 3-[4-(3-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 200 mg of the title compound. M.p. 175°-176° C. MS (70 eV): m/z 479 (M+, 0.5%), 254 (49), 225 (88), 209 (100), 182 (34).

後処理

  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

出典と根拠

ORDレコード
ord-32f0e1a47d884b0fa22a2aeb54b8e2e5
出典データセット
uspto-grants-1993_09
特許番号
US05246935

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