Hydrochloric Acid → 2-Chlorobenzenesulfonic acid 3-[(piperidin-4-yl)methoxy]phenyl ester
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])(=[O:24])=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1Participants
Procedure
2-Chlorobenzenesulfonic acid 3 -[[N-(tert-butoxycarbonyl)piperidin-4-yl]-methoxy]phenyl ester (565 mg, 1.2 mmol), as prepared in the preceding step, was treated with 30 mL of 4N HCl in 1,4-dioxan and stirred at room temperature for 2 h. After removing the solvent in vacuo, the residue was purified by flash column chromatography (5% methanol in methylene chloride to 5% methanol in methylene chloride saturated with NH3) to give the title compound as a white foam (360 mg, 79%). 1H-NMR (300 MHz, CDCl3) δ 1.50 (m, 2H), 1.91 (m, 3H), 2.77 (t, 2H), 3.33 (d, 2H), 3.73 (d, 2H), 4.44 (bs, 1H), 6.69 (m, 2H), 6.77 (dd, 1H), 7.16 (t, 1H), 7.37 (t, 1H), 7.62 (m, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C18H20NO4SCl: 382.1 (M+H), 404.1 (M+Na). Found: 382.1, 404.5.
Workup
- customAfter removing the solvent in vacuo
- customthe residue was purified by flash column chromatography (5% methanol in methylene chloride to 5% methanol in methylene chloride saturated with NH3)
Sources & evidence
- ORD record
- ord-d3f0631c4bde498884690ef43d603cda
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05792769
Reaction notes
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