Hydrochloric Acid → 2-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester

HRID 482091Notes

Reaction equation

HRID 482091 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([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:19]=[C:20]([CH3:22])[CH:21]=2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([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:19]=[C:20]([CH3:22])[CH:21]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 541653922-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)piperidin-3-yl]methoxy]-5-methylphenyl ester

Product 1

HCID 536550322-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl esterYield 95.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)piperidin-3-yl]methoxy]-5-methylphenyl ester (745 mg, 1.5 mmol), as prepared in the preceding step, was treated with 20 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 colorless syrup (565 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ 1.45 (t, 1H), 1.94 (m, 3H), 2.23 (s, 3H), 2.45 (bs, 1H), 2.77 (t, 2H), 3.50 (dd, 2H), 3.76 (m, 2H), 6.46 (d, 1H), 6.55 (d, 2H), 7.40 (dd, 1H), 7.62 (m, 2H), 7.96 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19 H22NO4SCl: 396.1 (M+H), 418.1 (M+Na), Found: 395.8, 418.2.

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-898f548122a54174ae97ca86dbc8ccf8
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

Loading…