Triethylamine → 4-(6-Hydroxy-hexylcarbamoyloxy)-piperidine-1-carboxylic acid benzyl ester

Participants

Reaction Steps

A solution of the carbonate (128.826 g, 0.322 moles) produced in Example 21 in 450 ml of methylene chloride was added dropwise under nitrogen to a solution of 6-amino-1-hexanol (56.6 g, 0.483 moles) and triethylamine (224.2 ml, 1.61 moles) in 2 L of methylene chloride at room temperature. After the addition the reaction was stirred overnight at room temperature. By TLC the reaction was not complete. An additional 37.7 g (0.322 moles) of 6-amino-1-hexanol and 224.2 ml (1.61 moles) of triethylamine were added and the stirring continued overnight. By TLC the reaction was complete. The reaction was extracted two times with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 95.0 g (78%) of a yellow oil which crystallized on standing, mp 50-52° C.

Provenance & Evidence