Dimethylamine → Ethyl N-(3,4-dichlorobenzyl)-4-dimethylaminomethyl-5-hydroxyindole-2-carboxylate

Participants

Reaction Steps

To a stirred solution of ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate (2.1 g) in ethanol (50 ml) was added successively aqueous dimetylamine (40%, 0.5 ml) and aqueous formaldehyde (0.5 ml). The solution was allowed to stand overnight and the resulting crystals filtered and dried in vacuo to give the product as pale yellow crystals (1.7 g, 70%); NMR δ(CD3SOCD3) 1.24 (t, 3H), 2.23 (s, 6H), 3.81 (s, 2H), 4.24 (q, 2H), 5.75 (s, 2H), 6.82 (d, 1H), 6.90 (dd, 1H), 7.30 (m, 3H), 7.50 (d, 1H); M/z (+) 423.421 (MH−), 378, 376.

Provenance & Evidence