Triethylamine → HCID 19850838, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.8 g, 5 mmol) and triethylamine (0.51 g, 5 mmol) in dry acetonitrile (25 ml), heated to 70° C., was added half of a solution of methyl-2-(bromomethyl)benzoate (1.15 g, 5 mmol) and triethylamine (0.51 g, 5 mmol) in acetonitrile (25 ml) over 0.5 hr. After 1.5 hr, the remainder of the solution was added slowly over 2 hr and stirred for a further 1 hr. After cooling and filtration the concentrated filtrate was chromatographed (silica gel, ether) to give a methyl-2-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]benzoate (0.66 g, 28%) as an oil. To this, in methanol (30 ml), was added 15% sodium hydroxide solution (8 ml) and the mixture was stirred for 3 hr. The solvent was removed in vacuo, water was added and the pH was adjusted to 6 with 2N HCl to give, after recrystallisation from IPA, 2-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]benzoic acid, H2O, 0.6HCl, 0.48(CH3)2CHOH.

Provenance & Evidence