Hydrochloric Acid → HCID 60770780, compound

HRID 748514Notes

Reaction equation

HRID 748514 reaction equation
[CH3:1][CH:2]([CH3:11])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[Cl:12][C:13]1[N:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.Cl>C(Cl)Cl>[Cl:12][C:13]1[N:18]=[CH:17][C:16]([S:19]([N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH:2]([CH3:11])[CH3:1])[CH2:6][CH2:7]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 100577581-(3-methylbutyl)piperazine

Product 1

HCID 60770780HCID 60770780, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(3-methylbutyl)piperazine (0.41 g, 2.60 mmol; described in: Yamane, T. et al. Chem. Pharm. Bull. 1993, 41, 148-155) in methylene chloride (15 mL) cooled on an ice-bath was 6-chloropyridine-3-sulfonyl chloride (0.50 g, 2.36 mmol; described in: Naegeli, C. et al. Helv. Chim. Actal. 1938, 21, 1746-1750) dissolved in methylene chloride (10 mL) added slowly. The reaction was stirred for 30 min and a 5% HCl(aq) solution (30 mL) was added and the phases were separated. The aqueous layer was alkalyzed with a saturated aqueous NaHCO3 solution until pH 9 and the mixture was extracted with methylene chloride. The organic layers were combined, dried (Na2SO4) and the solvent was removed in vacuo affording 650 mg (83% yield) of the title compound as a white solid: 1H NM (CDCl3, 400 MHz) δ 8.75 (d, J=2 Hz, 1 H), 7.97 (dd, J=8, 2 Hz, 1 H), 7.51 (d, J=8 Hz, 1 H), 3.33-3.05 (m, 4 H), 2.86-2.29 (m, 6 H), 1.66-1.50 (m, 1 H), 1.5-1.28 (m, 2 H), 0.88 (d, J=7 Hz, 6 H); MS (ES) mz 332 (M++1).

Workup

  1. additionadded slowly
  2. customthe phases were separated
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3f4169f072d145bea84d3c58c65bce0f
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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