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Progress of the reaction of dry HCl with indole base 9 (1H NMR, CDCl3, 300 MHz) to form N4-methyltalpinine (12). 1H NMR of (a) 9, (b) 9 + HCl (cat.), (c) 9 + HCl (2 eq) immediately after addition, and (d) 9 + HCl (2 eq) after 2 h. The star symbols mark the positions of changes in important signals.
