3-dodecoxypropan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 271 g (0.66 mol) of 1-hydroxy-4-ethoxycarbonylmethyloxy-2-naphthoic acid 4-nitrophenyl ester and 160 g (0.66 mol) of 3-n-dodecyloxypropylamine were added to 750 ml of tetrahydrofuran, and the mixture was stirred for 3 hours. 2 liters of water were added to the reacting solution, and extraction was carried out with 1 liter of ethyl acetate. After removal of ethyl acetate by distillation, the residue was dissolved in 1 liter of methanol, and cooled. The precipitated crystals were filtered off and dried to obtain 205 g (66% yield) of 1 -hydroxy-4-ethoxy-carbonylmethyloxy-N-(3-n-dodecyloxypropyl)-2-naphthamide. Melting point: 66°-67.5° C. After removal of ethyl acetate by distillation the residue was dissolved in 1 liter of methanol cooled The precipitated crystals were filtered off dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After adding 90.8 g of dicyclohexylcarbodiimide to a mixture of 150 g (0.400) of 4-chloromethyl-5-phenyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one prepared in the above step and 600 ml of chloroform, the reaction was performed for 30 minutes at room temperature. Then, 97.4 g of 3-dodecyloxypropylamine was added dropwise to the reaction mixture and thereafter, the reaction was further performed for 5 hours. The reaction product was purified by a short column of silica gel and the product was recrystallized from acetonitrile to provide 78.0 g of the desired product with a yield of 33.4%. The melting point thereof was 110° C. to 111° C. the reaction was further performed for 5 hours The reaction product was purified by a short column of silica gel the product was recrystallized from acetonitrile