tetradecan-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:

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: 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:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a reactor of the type used in Example 1 is charged a cold solution of N,N-dimethylchloramine (0.87 moles), chilled to -77° C, in 300 ml of methylene chloride, followed by aluminum chloride (0.3 moles). The mixture is stirred for 5 minutes and then diethyl ether (0.4 moles) is added. After stirring for an additional 5 minutes, an additional portion of diethyl ether (0.4 moles) and 1-tetradecene (0.3 mol) is added to the stirred solution. The chilled reaction mixture is heated to -35° C and the reaction mixture stirred for one hour. At the end of this time an 80 g portion of hydrochloric acid (28% by weight) and 100-300 g of water are added to the reaction mixture and stirred for a half hour. The organic and water layers are then separated and the organic layer is stirred for an additional half-hour with 80 g of the same strength hydrochloric acid used previously. Again the organic and water layers are separated. The organic layer is filtered to yield 0.02 mol of tetradecyl amine salt. This represents a 6.68% yield based on the amount of 1-tetradecene charged. To a reactor of the type used in Example 1 After stirring for an additional 5 minutes The chilled reaction mixture the reaction mixture stirred for one hour stirred for a half hour The organic and water layers are then separated the organic layer is stirred for an additional half-hour with 80 g of the same strength hydrochloric acid Again the organic and water layers are separated The organic layer is filtered

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

Procedure: 5 g (47 mmol) of anhydrous sodium carbonate are added to a solution of 10.0 g (47 mmol) of n-tetradecylamine in 100 ml of absolute acetone, and the suspension is heated to reflux. At that temperature 5.9 g (50 mmol) of propargyl bromide in 50 ml of acetone are then added dropwise and the mixture is subsequently heated at reflux for 2 hours. After aqueous working-up, the product is obtained in the form of a brown oil having a purity of >90%. the suspension is heated to reflux the mixture is subsequently heated at reflux for 2 hours After aqueous working-up, the product is obtained in the form of a brown oil

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

Procedure: 2,4-Dimethyl-6-tetradecylpyrylium hexafluorophosphate (10, n=13, 1.5 g, 3.33 mmol) was dissolved in 15 mL chloroform and treated with 0.71 g (3.33 mmol) of tetradecylamine (11, m=13). Triethylamine (0.5 mL) was then added to the brown-yellow solution, which was subsequently refluxed for 5 minutes, treated with 1 mL of acetic acid and refluxed for another hour. The homogenous mixture was treated with 0.2 mL of concentrated aqueous ammonia, refluxed for 5 min., cooled and extracted with 10 mL of water to solve the precipitated inorganic salts. After separation, the chloroform layer was dried on sodium sulfate and evaporated to dryness to yield 2.00 g of crude product. This product was purified by means of flash chromatography (Silica gel 60) using a 20/80 methanol/chloroform (v/v) mobile phase to yield 0.56 g (22%) of pure product, which was recrystallized from ethanol to yield 0.54 g of crystalline compound (12, m=n=13). was subsequently refluxed for 5 minutes refluxed for another hour refluxed for 5 min. cooled extracted with 10 mL of water After separation the chloroform layer was dried on sodium sulfate evaporated to dryness to yield 2.00 g of crude product This product was purified by means of flash chromatography (Silica gel 60)

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

Procedure: 2,4-Dimethyl-6-tetradecylpyrylium hexafluorophosphate (10, n=13, 1.5 g, 3.33 mmol) was dissolved in 15 mL chloroform and treated with 0.71 g (3.33 mmol) of tetradecylamine (11, m=13). Triethylamine (0.5 mL) was then added to the brown-yellow solution, which was subsequently refluxed for 5 minutes, treated with 1 mL of acetic acid and refluxed for another hour. The homogenous mixture was treated with 0.2 mL of concentrated aqueous ammonia, refluxed for 5 min., cooled and extracted with 10 mL of water to solve the precipitated inorganic salts. After separation, the chloroform layer was dried on sodium sulfate and evaporated to dryness to yield 2.00 g of crude product. This product was purified by means of flash chromatography (Silica gel 60) using a 20/80 methanol/chloroform (v/v) mobile phase to yield 0.56 g (22%) of pure product, which was recrystallized from ethanol to yield 0.54 g of crystalline compound (12, m=n=13). was subsequently refluxed for 5 minutes refluxed for another hour refluxed for 5 min. cooled extracted with 10 mL of water After separation the chloroform layer was dried on sodium sulfate evaporated to dryness to yield 2.00 g of crude product This product was purified by means of flash chromatography (Silica gel 60)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.1 g of 2-(benzyloxycarbonylamino)-2-deoxy-D-glucose were dissolved in 40 ml of dimethylformamide, 3.2 g of tetradecylamine were added and the mixture was warmed at 80° C. for 4 hours, under a water pump vacuum. The mixture was cooled to room temperature, diluted with 50 ml of tetrahydrofuran and stirred in the presence of 5 ml of ion exchanger SC 108 (H+ form). The exchanger resin was filtered off and 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate. After the mixture had been stirred for five hours, the solid constituents were filtered off and the filtrate was evaporated in vacuo. The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1). The mixture was cooled to room temperature The exchanger resin was filtered off 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate the solid constituents were filtered off the filtrate was evaporated in vacuo The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.1 g of 2-(benzyloxycarbonylamino)-2-deoxy-D-glucose were dissolved in 40 ml of dimethylformamide, 3.2 g of tetradecylamine were added and the mixture was warmed at 80° C. for 4 hours, under a water pump vacuum. The mixture was cooled to room temperature, diluted with 50 ml of tetrahydrofuran and stirred in the presence of 5 ml of ion exchanger SC 108 (H+ form). The exchanger resin was filtered off and 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate. After the mixture had been stirred for five hours, the solid constituents were filtered off and the filtrate was evaporated in vacuo. The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1). The mixture was cooled to room temperature The exchanger resin was filtered off 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate the solid constituents were filtered off the filtrate was evaporated in vacuo The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1)