Formaldehyde → N,N-Dimethyl-2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine

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Reaction Steps

0.058 mmol of 2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine (example 1) were dissolved in 2 ml of methanol. A solution of formaldehyde (0.351 mmol, 37%) and 0.351 mmol of sodium cyanotrihydroborate were added and the mixture was stirred at room temperature over night. H2O was added to the reaction mixture and the aqueous phase was extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and filtered. The filtrate was concentrated to 6 mg of crude solid material. The solid was washed with diisopropyl ether and dissolved in methanol. An equimolar amount of 1 N HCl was added and the volatiles removed in vacuo. The residue was washed with diethyl ether, dissolved in H2O, acidified with 1 N HCl and washed with additional diethyl ether. The aqueous phase was freeze dried to give 4.6 mg of the desired product (16.5%).

Provenance & Evidence