Bis(trimethylsilyl)carbodiimide → HCID 58424486, compound

Participants

Reaction Steps

To a solution of 3-(1′-acetyl-4-oxospiro[chroman-2,4′-piperidine]-6-yl)benzonitrile (60 mg, 0.167 mmol) in anhydrous DCM (5 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.35 mL, 0.35 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.086 mL, 0.367 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was quenched with ice-water (5 g), and stirred for 20 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted 2 times with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give N-(1′-acetyl-6-(3-cyanophenyl)spiro[chroman-2,4′-piperidine]-4-ylidene)cyanamide as light brown solid which was used for next step without further purification. MS ESI+ve m/z 385 (M+H)+.

Provenance & Evidence