Dimethylamine → HCID 178483562, compound

Participants

Reaction Steps

A solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-propyl ester (1.02 g, 1.89 mmol) in 2.0 M dimethylamine in THF (20 mL, 40 mmol) was stirred for 16 hours at 70° C. in a sealed tube. After cooling to ambient temperature, the reaction mixture was concentrated and partitioned in chloroform and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 0.5% ammonium hydroxide/5.0% methanol in chloroform. Dimethyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine was obtained as a light yellow solid (0.453 g, 58.5%). Methanol and ethereal hydrochloride were then added to this compound. The resulting solution was concentrated and dried for 14 hours at 84° C. in vacuo. Dimethyl-{3-[3-(naphthalene -1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine hydrochloride as a very light yellow solid (0.455 g) was obtained: MP: 264-5° C.; Mass Spectrum (−EI, [M−H]−) m/z 408.

Provenance & Evidence