1-Phenylpiperazine → HCID 58808535, compound

HRID 1921382Notes

Reaction equation

HRID 1921382 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16]([N:29]3[CH2:30][CH2:31][N:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:27][CH2:28]3)(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8857Ethyl AcetateHCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

Product 1

HCID 58808535HCID 58808535, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride (70 mg, 0.22 mmol) in methylene chloride (5 mL) is added 1-phenylpiperazine (30 mg, 0.22 mmol), piperidinomethyl polystyrene (75 mg, 0.262 mmol) and the mixture is stirred overnight at room temperature under a nitrogen atmosphere. After the reaction is completed (determined by TLC) it is filtered and the filtrate concentrated. The residue is purified by chromatography on a 5 g silica gel cartridge (eluting with ethyl acetate-50% heptane then 100% ethyl acetate) affording the corresponding sulfonamide as a solid (95% yield). LC/MS: RT 3.79 min; m/e 444 (M+H); 1H NMR (δ, ppm): 11.83 (1H, s), 7.65 (1H, d); 7.38 (1H, s); 7.28 (1H, d), 7.21 (2H, m), 6.94 (2H, d), 6.81 (1H, t), 3.26 (4H, br d), 3.12 (4H, br d), 2.38 (2H, q), 2.32 (3H, s), 1.09 (3H, t).

Workup

  1. filtrationis filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue is purified by chromatography on a 5 g silica gel cartridge (
  4. washeluting with ethyl acetate-50% heptane

Sources & evidence

ORD record
ord-f122cacb7caa4b84b1ba27eaecdd98b0
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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