Simple and efficient Decarboxylation of L-Tryptophan to Tryptamine in Acetophenone

DavidNichols

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Reagents:
  • L-Tryptophan 31g (152 mmol);
  • Acetophenone 100ml;
  • Acetone anhydrous 8ml;
  • Distilled water 300mL;
  • Hydrochloric acid (conc. HCl 37%) 13 mL;
  • Benzene ~300 mL;
  • Methylene chloride 100 mL;

L-tryptophan, acetophenone and Acetone was mixed in flask. Heated and stirred it until boiling under reflux (water coolling not needed) and kept it boiling roughly for 1 minute. CO2 production stopped and solution becomes clear orange. Reaction took about 10 minutes. Solution was colled, mixed with 150ml of cooled benzene and extracted with 3 portions of HCl dissolved in water (first 10ml of conc. HCL in 100ml, second 2ml in 50ml, third 1ml in 30ml). Water extracts were washed with benzene, turned into base with KOH, extracted twice with 50ml of DCM and dried under vacuum. Yield: 12.1g of crystalized tryptamine base (75,5 mmol; ~50%).
 

HerrHaber

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make's sense, I presume benzene can be replaced by toluene or xylenes in this instance due to both supply toxicity concerns
 
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