Triethylamine → HCID 69270089, compound

Participants

Reaction Steps

A solution of β-aminocrotononitrile (12 g, 147 mmol) and NEt3 (37 mL, 266 mmol) in CH2Cl2 (150 mL) was cooled with an ice bath to 0°. TiCl4 (7.9 mL, 72 mmol) in CH2Cl2 (100 mL) was added slowly with stirring followed by N-benzyl-4-piperidone (21.4 mL, 120 mmol) in one portion. The mixture was stirred for 24 h at ambient temperature and the volatiles were removed under reduced pressure. Ethly ether (400 mL) was added, and the resulting mixture was stirred vigorously until the residue was ground to a fine powder. The powder was filtered off and washed with ethyl ether (400 mL) and evaporation of the solvent afforded (E)-3-amino-2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-but-2-enenitrile as an oil (20 g, 70%), which was used without further purification.

Provenance & Evidence