Reaktion #10570

Reaktionsgleichung

2-Mesitylenesulfonyl chloride

4-piperidine-ethanol

→

N,O-Bis(2,4,6-trimethylbenzenesulfonyl)-4-piperidineethanol

Lösungsmittel

pyridine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigerose to −11° C
2. 2
   Filtration16.00 g (75%) of (2) as a yellow solid was filtered off

Vorschrift

2-Mesitylenesulfonyl chloride (24.78 g, 0.113 mol) in pyridine (60 ml) was added all at once to 4-piperidine-ethanol (5.58 g, 43.2 mmol) in pyridine (25 ml) at −16° C.; the temperature rose to −11° C. The flask was stored in the refrigerator at 5.5° C. for 44 hours under argon. The reaction mixture was poured into ice (1 kg) and after 3 hours, 16.00 g (75%) of (2) as a yellow solid was filtered off: mp 93.5-94° C.; NMR (CDCl3/TMS) δ 1.4-2.1 (m, 7H), 2.27 (s, 6H), 2.44-2.96 (m+s, 14H), 3.37-3.69 (m, 2H), 3.97 (t, 2H, J=5), 6.90 and 6.93 (2s, 4H). Anal. calcd. for C25H35NO5S2: C—60.82, H—7.15, N—2.84. Found: C—60.90, H—7.13, N—2.85.

Quelle