Hydrochloric Acid → 2-Chlorobenzenesulfonic acid 3-[2-(piperazin-4-yl)ethoxy]-5-methylphenyl ester

HRID 482095Notes

Reaction equation

HRID 482095 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([O:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])(=[O:27])=[O:26])[CH:20]=[C:21]([CH3:23])[CH:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([O:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])(=[O:27])=[O:26])[CH:20]=[C:21]([CH3:23])[CH:22]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 542578882-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)-piperazin-4-yl]ethoxy]-5-methylphenyl ester

Product 1

HCID 539792122-Chlorobenzenesulfonic acid 3-[2-(piperazin-4-yl)ethoxy]-5-methylphenyl esterYield 84.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)-piperazin-4-yl]ethoxy]-5-methylphenyl ester (1.02 g, 2.0 mmol), as prepared in the preceding step, was treated with 40 mL of 4N HCl in 1,4-dioxane at room temperature for 2 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography (10% methanol in methylene chloride saturated with NH3) to give the title compound as a pale-yellow liquid (695 mg, 84%). 1 H-NMR (300 MHz, CDCl3): δ 1.92 (bs, 2H), 2.24 (s, 3H), 2.53 (d, 3 H), 2.73 (t, 2H), 2.92 (t, 4H), 3.98 (t, 2H), 6.50 (t, 1H), 6.54 (t, 1H), 6.61 (t, 1H) 7.38 (dt, 1H), 7.62 (m, 2H), 7.97 (dd, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography (10% methanol in methylene chloride saturated with NH3)

Sources & evidence

ORD record
ord-c5aab8b739c143708b1677a3f29c9864
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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