Hydrochloric Acid → 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid hydrochloride salt

Participants

Reaction Conditions

Reaction Steps

To methyl 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylate (0.44 g, 1.363 mmol) was added 6 N HCl (20 ml, 120 mmol). The reaction was purged with N2, attached a reflux condensor, heated to 80° C., and stirred for 18 hr. LCMS showed that the reaction was complete. The reaction was cooled to RT, diluted with an equal volume of water, washed with EtOAc, and evaporated to dryness under vacuum to give the product 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid hydrochloride salt (0.42 g, 1.216 mmol, 89% yield) as a beige solid. (86% pure by LCMS, contains ˜10% of the des-chloro side product from the previous reaction.) Used as is in the next step. 1H NMR (400 MHz, DMSO-d6) δ=13.19 (br. s., 1 H), 10.45 (br. s., 1 H), 7.90 (d, J=1.8 Hz, 1 H), 7.33 (d, J=1.8 Hz, 1 H), 4.91 (quin, J=6.9 Hz, 1 H), 4.58 (d, J=5.6 Hz, 2 H), 2.79 (d, J=4.8 Hz, 6 H), 2.34 (s, 3 H), 1.58 (d, J=6.8 Hz, 6 H). MS(ES)+m/e 309.2 [M+H]+, 264.1 [M+H]+ −45 (HNMe2).

Provenance & Evidence