2-Chlorobenzenesulfonic acid 3-[2-[N-(tert-butoxycarbonyl)piperazin-4-yl]ethoxy]phenyl ester → 2-Chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl ester

HRID 482093Notes

Reaction equation

HRID 482093 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:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl>[N:11]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([O:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 542467972-Chlorobenzenesulfonic acid 3-[2-[N-(tert-butoxycarbonyl)piperazin-4-yl]ethoxy]phenyl ester

Product 1

HCID 178803862-Chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl esterYield 88.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Chlorobenzenesulfonic acid 3-[2-[N-(tert-butoxycarbonyl)piperazin-4-yl]ethoxy]phenyl ester (994 mg, 2.0 mmol), as prepared in the preceding step, was treated with 4N HCl (40 mL in 1,4-dioxane) and stirred at room temperature for 2 h. After concentrating in vacuo, the residue was purified by flash column chromatography (10% methanol in methylene chloride saturated with NH3) to give the title compound as a white foam (705 mg, 88%). 1H-NMR (300 MHz, CDCl3) δ 2.00 (bs, 1H), 2.54 (t, 4H), 2.76 (t, 2H), 2.93 (t, 4H), 4.02 (t, 2H), 6.72 (m, 2H), 6.78 (dd, 1H), 7.16 (t, 1H), 7.37 (dt, 1H), 7.61 (m, 2H), 7.95 (dd, 1H). Mass spectrum MALDI-TOF, sinapinic acid matrix) calcd. for C18H21N2O4SCl: 397.1 (M+H). Found: 397.6.

Workup

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

Sources & evidence

ORD record
ord-3d5384fe5f7746ffb557b62737af87a1
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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