Propanal → HCID 20426685, compound

Participants

Reaction Conditions

Reaction Steps

Alternatively, 0.5 g of dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthalenecarboxamide were dissolved in 100 ml. of a 1:1 THF/ethanol solvent mixture. About 1 g. of Raney nickel were added and the mixture stirred at about 0° C. while 5 ml. of hydrazine hydrate were added thereto in dropwise fashion. After the addition had been completed, the reaction mixture was stirred for 4 hours at ambient temperature after which time it was filtered. The solvent was removed from the filtrate leaving a yellow residue. TLC indicated a single spot with Rf =0.63 using a 63:7:27:3 chloroform/methanol/acetone/ammonium hydroxide solvent system. Yield of dl-2-benzyloxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide was 0.46 g. (100%). This 0.46 g. sample was alkylated with propionaldehyde and sodium cyanoborohydride by the procedure of Example 1 to yield dl-2-benzyloxy-6-di-n-propylamino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride. TLC (9:1 chloroform/methanol) Rf =0.40.

Provenance & Evidence