Chloroacetaldehyde → 2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

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Reaction Steps

5-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (7 g, Example 29b) and chloroacetaldehyde (50% solution in water, 6.6 ml) were stirred in methanol (120 ml) under nitrogen for 10 min. A mixture of 6M hydrochloric acid (1.8 ml) and methanol (1.8 ml) was added, followed by sodium cyanoborohydride (1.48 g). The mixture was stirred for 2.5 h. The methanol was then removed under reduced pressure and the residue partitioned between saturated aqueous sodium hydrogencarbonate and dichloromethane The aqueous layer was extracted twice more with dichloromethane and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the sub-title compound (8.2 g).

Provenance & Evidence