Piperazine → HCID 131728443, compound

HRID 1927461Notes

Reaction equation

HRID 1927461 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:10]=3[S:11](=[O:14])(=[O:13])[CH2:12][C:6]=2[CH:5]=[C:4]([S:23](Cl)(=[O:25])=[O:24])[CH:3]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[CH2:33](OC(=O)C)C>>[CH3:33][O:22][C:20]([C:16]1[CH:17]=[C:18]([CH3:19])[C:9]2[O:8][C:7]3[C:2]([Cl:1])=[CH:3][C:4]([S:23]([N:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)(=[O:25])=[O:24])=[CH:5][C:6]=3[CH2:12][S:11](=[O:14])(=[O:13])[C:10]=2[CH:15]=1)=[O:21]

Participants

4

Reactant 3

HCID 4837PiperazineHCID 8857Ethyl AcetateHCID 131728441HCID 131728441, compound

Product 1

HCID 131728443HCID 131728443, compound

Procedure

A suspension of Example 49j (0.5 g, 1.14 mmol) in ethylacetate (20 mL) was treated with piperazine (0.147 g, 1.7 mmol) at room temperature and allowed to stir overnight. It was concentrated, treated with methanolic-HCl (50 mL) and refluxed overnight. The reaction mixture was concentrated, treated with an aqueous sodium bicarbonate solution and extracted with n-butanol. The organic layer was washed with water, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound. Yield: 0.2 g, (35%); 1H NMR (DMSO-d6): δ 2.8 (s, 3H, CH3), 2.9 (s, 4H, 2CH2), 3.2 (s, 4H, 2CH2), 3.89 (s, 3H, OCH3), 5.51 (s, 2H, CH2), 8.10 (s, 1H, Ar), 8.21 (s, 1H, Ar), 8.30 (s, 2H, Ar); MS: m/e (ES−) 499 (M−1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with methanolic-HCl (50 mL)
  3. temperaturerefluxed overnight
  4. concentrationThe reaction mixture was concentrated
  5. additiontreated with an aqueous sodium bicarbonate solution
  6. extractionextracted with n-butanol
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-3d6e48464bf14f789bfa30443f3d031e
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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