ditetradecylamine

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

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

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-myristyl myristamide (0.90 g; 2.1 mmole) was treated with borane THF (5 mL of 1 M solution, 5.0 mmole) and reacted at reflux for 3 hrs. The reaction mixture was carefully neutralized with 3N HCl aqueous solution and stirred at 50° C. for 20 min., the back neutralized with 2N NaOH aqueous solution. The mixture was concentrated, then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution, dried and concentrated, affording 0.93 g of product. NMR (CDCl3): δ2.59 (t, 2H, J=7.2 Hz), 1.40-1.55 (m, 2H), 1.15-1.40 (m, 22H), 0.88 (t, 3H, J=6.8 Hz). reacted at reflux for 3 hrs The mixture was concentrated partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution dried concentrated

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

Procedure: N-myristyl myristamide Myristoyl chloride (2.5 g; 10 mmole) was added to a room temperature methylene chloride solution of n-tetradecylamine (2.1 g; 10 mmole, TCI chemicals) and DBU (2.3 g; 15 mmole). The resulting mixture was stirred at room temperature for 4 hours, diluted with CH2Cl2, washed with brine solution, dried, and purified by column chromatography on silica gel, to give 3.40 g, 80.9% of product. 1H NMR (CDCl3): δ5.38 (6s, 1H), 3.24 (q, 2H), 2.16 (t, 2H, J=7.8 Hz), 1.58-1.66 m, 2H), 1.40-1.57 (m, 2H), 1.20-1.40 (m, 42H), 0.89 (t, 6H). washed with brine solution dried purified by column chromatography on silica gel

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-myristyl myristamide (0.90 g; 2.1 mmole) was treated with borane THF (5 mL of 1 M solution, 5.0 mmole) and reacted at reflux for 3 hrs. The reaction mixture was carefully neutralized with 3N HCl aqueous solution and stirred at 50° C. for 20 min., the back neutralized with 2N NaOH aqueous solution. The mixture was concentrated, then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution, dried and concentrated, affording 0.93 g of product. NMR (CDCl3): δ2.59 (t, 2H, J=7.2 Hz), 1.40-1.55 (m, 2H), 1.15-1.40 (m, 22H), 0.88 (t, 3H, J=6.8 Hz). reacted at reflux for 3 hrs The mixture was concentrated partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution dried concentrated

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

Procedure: N-myristyl myristamide Myristoyl chloride (2.5 g; 10 mmole) was added to a room temperature methylene chloride solution of n-tetradecylamine (2.1 g; 10 mmole, TCI chemicals) and DBU (2.3 g; 15 mmole). The resulting mixture was stirred at room temperature for 4 hours, diluted with CH2Cl2, washed with brine solution, dried, and purified by column chromatography on silica gel, to give 3.40 g, 80.9% of product. 1H NMR (CDCl3): δ5.38 (6s, 1H), 3.24 (q, 2H), 2.16 (t, 2H, J=7.8 Hz), 1.58-1.66 m, 2H), 1.40-1.57 (m, 2H), 1.20-1.40 (m, 42H), 0.89 (t, 6H). washed with brine solution dried purified by column chromatography on silica gel

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

Procedure: N-myristyl myristamide Myristoyl chloride (2.5 g; 10 mmole) was added to a room temperature methylene chloride solution of n-tetradecylamine (2.1 g; 10 mmole, TCI chemicals) and DBU (2.3 g; 15 mmole). The resulting mixture was stirred at room temperature for 4 hours, diluted with CH2Cl2, washed with brine solution, dried, and purified by column chromatography on silica gel, to give 3.40 g, 80.9% of product. 1H NMR (CDCl3): δ5.38 (6s, 1H), 3.24 (q, 2H), 2.16 (t, 2H, J=7.8 Hz), 1.58-1.66 m, 2H), 1.40-1.57 (m, 2H), 1.20-1.40 (m, 42H), 0.89 (t, 6H). washed with brine solution dried purified by column chromatography on silica gel

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: 12.65 mmol of succinic anhydride (1.266 g), 12.65 mmol of 4-dimethylaminopyridine (1.546 g) and 10.75 mmol of ditetradecylamine (4.407 g) were successively added to 125 ml of dichloromethane in a round-bottomed flask. The reaction mixture was stirred for 18 hours at room temperature. Once the reaction was complete, the mixture was extracted with dichloromethane and hydrochloric acid (1N). The organic phase was then washed with brine and dried over magnesium sulfate, filtered and then concentrated to give 4.21 g of product (3) (yield: 66%). the mixture was extracted with dichloromethane and hydrochloric acid (1N) The organic phase was then washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: 12.65 mmol of succinic anhydride (1.266 g), 12.65 mmol of 4-dimethylaminopyridine (1.546 g) and 10.75 mmol of ditetradecylamine (4.407 g) were successively added to 125 ml of dichloromethane in a round-bottomed flask. The reaction mixture was stirred for 18 hours at room temperature. Once the reaction was complete, the mixture was extracted with dichloromethane and hydrochloric acid (1N). The organic phase was then washed with brine and dried over magnesium sulfate, filtered and then concentrated to give 4.21 g of product (3) (yield: 66%). the mixture was extracted with dichloromethane and hydrochloric acid (1N) The organic phase was then washed with brine dried over magnesium sulfate filtered concentrated