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Synthesis of Tryptamine from Tryptophan
by Rhodium

The by far easiest method to synthesize tryptamine is the decarboxylation of the amino acid tryptophan. Both the natural form of tryptophan (L-tryptophan) as well as the synthetic form (DL-tryptophan) can be used with the same good results, both variants are fully interchangeable in thesyntheses below.
Purification of Tryptamine
A good way to purify tryptamine without having to resort to distillation under strong vacuum is to dissolve the crude tryptamine hydrochloride in water, adjust the pH to between 7.6 and 8.2 and extract the solution with chloroform. The pH is then adjusted to 14 with NaOH and the pure tryptamine is filtered off with suction and air dried.
ExperimentalDecarboxylation in Diphenyl Ether1
DL-Tryptophan (1.0 g) and diphenyl ether (50 ml) were heated at reflux for 1 hour in an atmosphere of nitrogen. The mixture was cooled and extracted with 2N aqueous hydrochloric acid (3x40ml). This extract was washed with ether, basified (6N NaOH), and extracted with ether (5x50ml). This extract was washed with water and brine, dried over sodium sulfate, and thesolvent removed in vacuo, leaving a residue which was recrystallized from benzene to give pale yellow prisms (530mg), mp 113-114°C. Sublimation afforded a colorless crystalline solid (450mg, 57%), mp 114-115°C.
The use of freshly distilled tetralin as the solvent for decarboxylation led to a yield of only 36%. With commercial tetralin the yield was reduced to 20%. No tryptamine was isolated fromexperiments which employed diphenylamine or dimethylsulfoxide in place of diphenyl ether.
Decarboxylation of Tryptophan in Diphenylmethane2
A suspension of L-tryptophan (250 mg) in warm diphenylmethane (10 g) was gently refluxed in a stream of nitrogen for 5-20 min until no more evolution of carbon dioxide was observed. After cooling, the clear pale yellow reaction mixture was treated with abenzene solution (20 ml) saturated with dry hydrogen chloride. The resulting precipitate was collected by filtration, washed with n-hexane and dried to afford crude tryptamine hydrochloride (223 mg, 93%) which was recrystallised from ethanol/ethyl acetate to yield tryptamine hydrochloride (151 mg, 63%) as colorless needles, mp 248-249°C.
Another similar procedure (unfortunately without reference),reads as follows:
A mixture of 0.3-0.5 g of DL-tryptophan and 12-20 g of diphenylmethane was boiled over a burner flame in an atmosphere of nitrogen for 20 min. After cooling, 20-40 ml of a saturated benzene solution of hydrogen chloride was added to the mixture. The precipitate of salts that deposited was separated off and was dissolved in a mixture of ethanol and ethyl acetate. On strong cooling,lustrous colorless crystals deposited with a mp 248-249°C. The experiment was repeated several times. Yield 75-90%.
Copper-catalyzed Decarboxylation of Tryptophan3

Tryptophan Copper Chelate
To a solution of L-tryptophan (50g) in water was added a solution of an excess of copper(II)acetate in water. The resultant precipitate was filtered. The extract was then washed several times with hot waterto give the copper chelate compound. Yield: 52g, mp >280°C.
Decarboxylation of the Tryptophan Copper Chelate
A suspension of Tryptophan Copper Chelate in DMSO was heated at 170-175°C for several minutes, during which time an evolution of carbon dioxide was observed. After cooling, the resultant precipitate was filtered and to the filtrate was added a suitable amount of water. The reactionmixture was made basic with 30% sodium hydroxide solution and extracted with chloroform. After distillation of the solvent, the resultant residue was purified by flash chromatography on silica gel to givce tryptamine in 40% yield. The use of HMPA (hexamethylphosphoric triamide) instead of DMSO increased the yield to 45%, but that small increase in yield is not worth working with the expensive and...