Reaktion #738707

Reaktionsgleichung

2-chlorobenzenesulfonic acid 1-[(piperidin-4-yl)methoxy]naphthalen-3-yl ester hydrochloride

ethyl acetimidate hydrochloride

N,N-diisopropylethylamine

N,N-diisopropylethylamine

ethyl acetimidate hydrochloride

→

title compound

2-Chlorobenzenesulfonic acid 1-[[(1-acetimidoyl)piperidin-4-yl]methoxy]naphthalen-3-yl ester acetic acid salt

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for another 4 h
2. 2
   EinengenThe reaction mixture was concentrated to dryness
3. 3
   Sonstigequenched with 1 N sodium hydroxide (2 mL)
4. 4
   Extraktionextracted into methylene chloride
5. 5
   Trocknendried (K2CO3)
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.ADDITIONThe residue was diluted with methylene chloride (1 mL)
8. 8
   workup.ADDITIONtreated with 1 mL of glacial acetic acid
9. 9
   Sonstigedirectly purified by preparative thin layer chromatography

Vorschrift

A mixture of 100 mg (0.214 mmol) of 2-chlorobenzenesulfonic acid 1-[(piperidin-4-yl)methoxy]naphthalen-3-yl ester hydrochloride, as prepared in the preceding step, in N,N-dimethylformamide (2 mL) containing 55 mg (0.45 mmol) of ethyl acetimidate hydrochloride and 125 μL of N,N-diisopropylethylamine was stirred at ambient temperature overnight. To the reaction mixture was added another 125 μL of N,N-diisopropylethylamine and 55 mg (0.45 mmol) of ethyl acetimidate hydrochloride. The reaction mixture was stirred for another 4 h. The reaction mixture was concentrated to dryness, quenched with 1 N sodium hydroxide (2 mL), extracted into methylene chloride, dried (K2CO3), and concentrated in vacuo. The residue was diluted with methylene chloride (1 mL), treated with 1 mL of glacial acetic acid and directly purified by preparative thin layer chromatography using methylene chloride/methanol/glacial acetic acid (93.6:6.5:0.5) as developing solvent to give the title compound. 1H-NMR (300 MHz, DMSO-d6) δ 8.14 (d, 1 H, J=8 Hz), 7.8-7.97 (m, 4 H), 7.50-7.59 (m, 3 H), 7.19 (s, 1 H), 6.68 (d, 1 H, J=2 Hz), 4.11 (d, 2 H, J=6 Hz), 3.92 (d, 2 H, J=6 Hz), 3.11 (t, 2 H, J=2.6 Hz), 2.2 (m, 1 H), 1.92 (d, 2 H), 1.75 (br s, 3 H), and 1.41 (q, 2 H). Mass spectrum (MALDI-TOF; α-cyano-4-hydroxycinnamic acid matrix) calcd. for C23H24ClN3O4S: 474.1 (M+H). Found: 473.8.

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