Indole N-alkylation of tryptamines via dianion and phthalimido intermediates. New potential indolealkylamine haptens

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Abstract
Tryptamine derivatives 3a–c and 4a, 4b, 4d have been converted into the indole N-p-carbomethoxybenzyl derivatives 1a, 1b, 1g, and 2a, 2b, 2c, respectively, using dianion and phase-transfer catalytic methodologies. Treatment of these compounds with lithium iodide and sodium cyanide in refluxing dimethylformamide gave the corresponding carboxylic acids 1d, 1e, 1h, and 2d, 2e, 2f. The serotonin analogue 1f was obtained by catalytic debenzylation of 1h. These products may be useful haptens for eliciting specific antibodies to indolealkylamines.

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