Ethanolamine → HCID 86603036, compound

Participants

Reaction Steps

3.24 g (20 mmol) of 4-tert-butyl benzaldehyde and 1.22 g (20 mmol) of ethanol amine were dissolved in 20 ml methanol and stirred at rt for 30 min. 740 mg (20 mmol) of sodium borohydride were added in portions under nitrogen and the reaction mixture was stirred for 1 h at rt after complete addition. The solvent was evaporated and the residue was dissolved in diethyl ether. The organic layer was washed twice with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was dissolved in 20 ml DCM and 3.22 g (20 mol) of 1H-indole-7-carboxylic acid and 3.82 g (20 mmol) of EDC.HCl were added. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was dissolved in EtOAc. The organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave a colorless oil, which on treatment with diethyl ether yielded 2.54 g (36%) product as a white solid after filtration and drying. MS (ISP) 351.3 (M+H)+.

Provenance & Evidence