N-methyltetradecan-1-amine

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

Procedure: A mixture of 19.2 grams 2-chloro-4-methyl-5-nitrobenzamide, 21.4 grams methyltetradecylamine and 46.0 ml triethylamine was heated on a steam bath for 20 hours. The mixture was poured into about 200 ml ice water and made acid with concentrated HCl to a pH of 2-3. The mixture was filtered, washed with water and vacuum dried. The crude material was recrystallized from ethanol to give 30 grams product. m.p. = 117°-119°. was heated on a steam bath for 20 hours The mixture was filtered washed with water and vacuum dried The crude material was recrystallized from ethanol

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

Procedure: A mixture of 24.5g 2-chloro-4-ethoxy-5-nitrobenzoic acid, 22.7g methyl tetradecylamine (distilled) and 35.0 ml triethylamine were heated on a steam bath for 5 hours and then poured into two liters of water and made acid with HCl. The reaction product was filtered and washed with water, and recrystallized twice from methanol/water. were heated on a steam bath for 5 hours The reaction product was filtered washed with water recrystallized twice from methanol/water

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

Procedure: A mixture of 600g 2-chloro-5-nitrobenzoic acid, 900g methyltetradecylamine (84%, tertiary amines as impurities) and 500 ml triethylamine was heated on a steam bath for 7 hours and then poured into 2 liters of water and made acid with HCl. The reaction product was filtered, air dried and then recrystallized from methanol and then from petroleum ether. Yield: 820g, m.p. = 100°-101°. was heated on a steam bath for 7 hours The reaction product was filtered air dried recrystallized from methanol