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

HRID 5858ノート

反応式

HRID 5858 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: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

参加物

4

反応物 2

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

生成物 1

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

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-(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).

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-7dae953e4f5249e8b8c29ff501f4aac0
出典データセット
uspto-grants-1993_09
特許番号
US05246935

反応ノート

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