1-Phenylpiperazine → 2-[2-(3,4-Dimethoxy-phenyl)-3-methylsulfanyl-benzofuran-5-yl)-1-(4-phenyl-piperazin-1-yl)-ethanone

HRID 2040494Notes

Reaction equation

HRID 2040494 reaction equation
C(N(CC)CC)C.[C:8]1([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:30]2[O:31][C:32]3[CH:40]=[CH:39][C:38]([CH2:41][C:42](O)=[O:43])=[CH:37][C:33]=3[C:34]=2[S:35][CH3:36])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>ClCCl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:30]2[O:31][C:32]3[CH:40]=[CH:39][C:38]([CH2:41][C:42]([N:17]4[CH2:18][CH2:19][N:14]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[CH2:15][CH2:16]4)=[O:43])=[CH:37][C:33]=3[C:34]=2[S:35][CH3:36])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 68473283[2-(3,4-Dimethoxy-phenyl)-3-methylsulfanyl-benzofuran-5-yl]-acetic acid

Product 1

HCID 684711512-[2-(3,4-Dimethoxy-phenyl)-3-methylsulfanyl-benzofuran-5-yl)-1-(4-phenyl-piperazin-1-yl)-ethanoneYield 554%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine and 12.992 mg of 1-phenyl-piperazine (0.080 mM) were added to the solution containing 35 mg of 3[2-(3,4-dimethoxy-phenyl)-3-methylsulfanyl-benzofuran-5-yl]-acetic acid (35a; 0.068 mM) dissolved in 2 ml of dichloromethane. The reaction mixture was stirred for 16 hours and the remaining solvent was removed. The remaining residue was purified with Silica gel column chromatography with a mobile phase (dichloromethane:methanol=20:1) to obtain white solid type of 2-[2-(3,4-dimethoxy-phenyl)-3-methylsulfanyl-benzofuran-5-yl)-1-(4-phenyl-piperazin-1-yl)-ethanone (37a; 223 mg).

Workup

  1. customthe remaining solvent was removed
  2. customThe remaining residue was purified with Silica gel column chromatography with a mobile phase (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-23b0553ecbde4f69808ff02f62390d19
Source dataset
uspto-grants-2013_11
Patent number
US08580848B2

Reaction notes

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