Triethylamine → Tryptamine

Participants

Reaction Conditions

Reaction Steps

These compounds were synthesized by a slightly modified reported procedure (2). Tryptamine hydrochloride salt (0.8 mmol) was dissolved in CH2Cl2 (10 mL) and cooled to 0° C. in an ice bath in a 100 mL round bottom flask. Et3N (3.2 mmol) was added dropwsie to the cold solution followed by addition of n-decanoyl chloride (1.6 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched by addition of water (10 mL) and extracted with CH2Cl2 (3×10 mL). The organic layer was then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with 100% hexanes and 20-30% EtOAc/hexanes to afford N-decanoylamide of tryptamine as an yellow solid (236 mg, 92%). Rf=0.5 (20% EtOAc/hexanes).

Provenance & Evidence