Triethylamine → HCID 14371870, compound

Participants

Reaction Steps

To a solution of (1-benzyl-4-carboxypiperidin-4-yl)acetic acid.hydrochloride (31.3 g) in dimethylformamide (200 ml) was added dicyclohexylcarbodiimide (20.6 g). The mixture was stirred for one hour at room temperature, to which were added benzyloxyamine hydrochloride (16 g) and triethylamine (14 ml). The mixture was stirred for further one hour at room temperature, followed by evaporating off the solvent under reduced pressure. To the residue were added acetic anhydride (150 ml) and sodium acetic anhydride (21 g). The mixture was stirred for one hour at 100° C., then insolubles were filtered off, and the solvent was evaporated off under reduced pressure. To the residue was added ethyl acetate (200 ml), to which was further added a saturated aqueous solution of sodium hydrogencarbonate until the aqueous layer became alkaline. The organic layer was washed with water, dried over anhydrous magnesium sulfate, followed by evaporating off the solvent under reduced pressure. To the residual oil was added 100 ml of acetonitrile, and insolubles were filtered off. Acetonitrile was evaporated off, and the residue was recrystallized from acetonitrile-ethyl ether to obtain 16.5 g of a colorless solid, m.p. 146° to 152° C.

Provenance & Evidence