Triethylamine → N1-(S-(4-methoxybenzyl)thiosalicyloyl)-N4-benzylpiperazine

HRID 1263477Notes

Reaction equation

HRID 1263477 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][S:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1.[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]([N:30]2[CH2:31][CH2:32][N:27]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:28][CH2:29]2)=[O:13])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 3568003Benzoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-

Product 1

HCID 69734254N1-(S-(4-methoxybenzyl)thiosalicyloyl)-N4-benzylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N1-(S-(4-methoxybenzyl)thiosalicyloyl)-N4-benzylpiperazine (compound 5) was prepared using the same procedure described above using: 10 mM(2.743 g) of S-(4-methoxybenzyl) thiosalicylic acid, 3 mM(728 mg) of 1-Benzylpiperazine and 20 mM (3.525 g)triethylamine. The product was dissolved in 5 ml of methylene chloride and purified by column chromatography on a silica gel column (eluent: Ethyl acetate) to give 870 mg(20.1%) of a white crystal. The product was then further purified by crystallization from hexane. The purified product had having a melting point of 84-85° C. and had the following specifications:

Workup

  1. custompurified by column chromatography on a silica gel column (eluent: Ethyl acetate)

Sources & evidence

ORD record
ord-f3417361f43040a5b46b5b184243cb1d
Source dataset
uspto-grants-2003_04
Patent number
US06541479B1

Reaction notes

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