Production method of N-allyl-n-(methoxycarbonyl)-1,3-decadiynylamine contains 3 steps. The synthetic routes are as follows:

A. N-(Methoxycarbonyl)-2-propenylamine. A 250-mL, three-necked, round-bottomed flask equipped with a magnetic stir bar, an argon gas inlet tube, a rubber septum, which is pierced with a -coated thermocouple, and a 200-mL pressure-equalizing addition funnel fitted with a rubber septum is charged via syringe through the septum with allylamine (14.0 mL, 10.68 g, 187 mmol, 2.1 equiv) and 100 mL of dichloromethane. The solution is cooled to 0 °C (internal temperature) in an ice-water bath and a solution of methyl chloroformate (7.0 mL, 8.6 g, 91 mmol) in 30 mL of dichloromethane is added dropwise via the addition funnel over 10 min. The resulting white mixture is allowed to warm to room temperature over 30 min and then transferred to a 500-mL separatory funnel and extracted with 50 mL of aqueous 1M HCl solution, 50 mL of saturated aqueous NaHCO₃ solution and 50 mL of saturated aqueous NaCl solution. The organic phase is dried over MgSO₄, filtered, and concentrated by rotary evaporation (23 °C, 16 mmHg) to afford 10.12–10.26 g (97–98%) of carbamate 2 as a colorless oil.

B. 1-Bromo-1,3-decadiyne. Into a 200-mL, round-bottomed flask equipped with a magnetic stir bar is added 1,3-decadiyne (5.66 g, 42.2 mmol) and 100 mL of acetone. The flask is equipped with a rubber septum and argon inlet needle. (8.26 g, 46.4 mmol, 1.1 equiv) and AgNO₃ (0.717 g, 4.22 mmol, 0.10 equiv) are each added in one portion through temporary removal of the septum. The rubber septum is replaced with an argon inlet adapter, the flask is wrapped with aluminum foil, and the reaction mixture is stirred at room temperature for 22 h. The resulting cloudy orange mixture is transferred to a 500-mL separatory funnel with the aid of 100 mL of pentanes and washed with two 50-mL portions of saturated aqueous Na₂S₂O₃ solution. The combined aqueous layers are extracted with two 50-mL portions of pentanes and the combined organic phases are washed with 100 mL of saturated NaCl solution, dried over MgSO₄, filtered, and concentrated by rotary evaporation (23 °C, 16 mmHg) to provide 8.18–8.25 g (91–92%) of bromodiyne 4 as a red oil.

C. N-(Methoxycarbonyl)-N-(2-propenyl)-1,3-decadiynylamide. Into a 500-mL, three-necked, round-bottomed flask is weighed carbamate 2 (3.98 g, 34.6 mmol). The flask is equipped with a large magnetic stir bar, an argon inlet adapter, rubber septum, and a 125-mL pressure-equalizing addition funnel fitted with a rubber septum. (130 mL) and pyridine (70 mL, 68.0 g, 867 mmol, 25 equiv) are added via syringe through the septum. The solution is cooled to 0 °C (internal temperature) in an ice-water bath and 38 mL of potassium hexamethyldisilazide solution (0.91 M in THF, 34.6 mmol, 1.0 equiv) is added via syringe over 10 min. The peach-colored slurry is allowed to warm to room temperature over 15 min and then copper(I) iodide (6.58 g, 34.6 mmol, 1.0 equiv) is added in one portion by temporarily removing the septum. The resulting yellow-green mixture is stirred at room temperature for 2 h. A solution of bromodiyne 4 (8.47 g, 39.8 mmol, 1.15 equiv) in 40 mL of THF is then added via the addition funnel over 45 min (5 mL THF rinse). The flask and addition funnel are wrapped with aluminum foil to protect the bromodiyne 4 from light and the resulting mixture is stirred at room temperature for 20 h. The dark red-brown reaction mixture is transferred to a 1-L separatory funnel, diluted with 150 mL of diethyl ether, and washed with four 100-mL portions of a 3:1 mixture of saturated NaCl solution and concentrated NH₄OH solution. The blue aqueous layers are extracted with two 100-mL portions of Et₂O, and the combined organic layers are washed with two 200-mL portions of 1M HCl solution, 200 mL of saturated NaCl solution, dried over MgSO₄, filtered, and concentrated by rotary evaporation (40 °C, 16 mmHg) to afford 18.5 g of dark red oil. This material is transferred to a column (12 × 8 cm) of 300 g of silica gel and eluted with 500 mL of hexanes. Elution is then continued with 5% EtOAc-hexanes and 50-mL fractions are collected. Fractions 14 to 51 are combined and concentrated by rotary evaporation (23 °C, 16 mmHg) to provide 6.88 g (80%) of diynamide 5 as a red oil.