Propane sultone → 1,2,3,4-Tetrahydroquinoline-N-propanesulphonic acid

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Reaction Steps

A mixture of 1,2,3,4-tetrahydroquinoline (4.76 g, 40 mmole) and 1,3-propane sultone (4.88 g, 40 mmole) in 50 mL reagent grade acetonitrile was heated under a nitrogen atmosphere and refluxed overnight. After cooling to room temperature, then to ice bath temperature, the resulting white solid was filtered and washed with cold acetonitrile. The yield was 8.1 g (84%), and the product had a melting point of greater than 200° C. Nuclear magnetic resonance (NMR) and elemental analysis showed the product to be consistent with the assigned structure. NMR (D2O): 7.45 (s, 4H), 2.8-4.0 (m, 8H), 2.2 (T, 2H).

Provenance & Evidence