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

HRID 5857

Reaction equation

HRID 5857 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-32f0e1a47d884b0fa22a2aeb54b8e2e5
Source dataset
uspto-grants-1993_09
Patent number
US05246935

Linked notes

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