N-(2-hydroxyethyl)hexadecanamide

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: 3.0 g of N-(2-hydroxyethyl) hexadecanamide (10 mmoles) was dissolved in 75 ml of tetrahydrofuran (THF) at 45° C. with stirring. 1.11 g of N-methylmorpholine (11 moles) and 1.19 g of ethyl chloroformate (11 moles) were added and the resulting mixture was stirred for a further 3 hours at ambient temperature. The mixture was then evaporated to dryness under vacuum. The residue was taken up with 50 ml of water and extracted 3 times with 30 ml of ethyl acetate; the organic phases were washed twice with 20 ml of water, recombined and evaporated to dryness. The residue was crystallized from 30 ml of tert-butylmethyl ether. The crystallizate was separated by filtration, washed twice with 5 ml of cold tert-butylmethyl ether and finally dried under a high degree of vacuum. The yield of the reaction was 93%. the resulting mixture was stirred for a further 3 hours at ambient temperature The mixture was then evaporated to dryness under vacuum extracted 3 times with 30 ml of ethyl acetate the organic phases were washed twice with 20 ml of water evaporated to dryness The residue was crystallized from 30 ml of tert-butylmethyl ether The crystallizate was separated by filtration washed twice with 5 ml of cold tert-butylmethyl ether finally dried under a high degree of vacuum

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

Procedure: 2-Aminoethanol (13.76 g, 225.3 mmol) was dissolved in CHCl3 (750 ml). To the solution was added dropwise palmitoyl chloride (15.48 g, 56.3 mmol) with stirring under ice cooling. Thereafter, the mixture was stirred at room temperature for 19 hours. Thereafter, the mixture was stirred at room temperature for 19 hours

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

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

Procedure: 2-Aminoethanol (13.76 g, 225.3 mmol) was dissolved in CHCl3 (750 ml). To the solution was added dropwise palmitoyl chloride (15.48 g, 56.3 mmol) with stirring under ice cooling. Thereafter, the mixture was stirred at room temperature for 19 hours. Thereafter, the mixture was stirred at room temperature for 19 hours

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

Procedure: In an exemplary embodiment, 20 mmol ethanolamine was reacted with 1 mmol vinyl stearate at 80° C. for 1 hour in the presence of 1% sodium methoxide. N-stearoylethanolamine with 96% purity was obtained after the removal of excess ethanolamine without further purification. In another exemplary embodiment, 20 mmol ethanolamine was reacted with 1 mmol vinyl palmitate at 60° C. for 1.5 hours in the presence of 1% sodium methoxide. N-palmitoylethanolamine with 98% purity was obtained after the removal of excess ethanolamine without further purification. More examples of reacting the alkanolamine and the vinyl ester of the fatty acid to prepare the high-purity fatty acid N-acylalkanolamine in a high yield are described in Examples 1-8. after the removal of excess ethanolamine without further purification

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

Procedure: 3.0 g of N-(2-hydroxyethyl) hexadecanamide (10 mmoles) was dissolved in 75 ml of tetrahydrofuran (THF) at 45° C. with stirring. 1.11 g of N-methylmorpholine (11 moles) and 1.19 g of ethyl chloroformate (11 moles) were added and the resulting mixture was stirred for a further 3 hours at ambient temperature. The mixture was then evaporated to dryness under vacuum. The residue was taken up with 50 ml of water and extracted 3 times with 30 ml of ethyl acetate; the organic phases were washed twice with 20 ml of water, recombined and evaporated to dryness. The residue was crystallized from 30 ml of tert-butylmethyl ether. The crystallizate was separated by filtration, washed twice with 5 ml of cold tert-butylmethyl ether and finally dried under a high degree of vacuum. The yield of the reaction was 93%. the resulting mixture was stirred for a further 3 hours at ambient temperature The mixture was then evaporated to dryness under vacuum extracted 3 times with 30 ml of ethyl acetate the organic phases were washed twice with 20 ml of water evaporated to dryness The residue was crystallized from 30 ml of tert-butylmethyl ether The crystallizate was separated by filtration washed twice with 5 ml of cold tert-butylmethyl ether finally dried under a high degree of vacuum

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

Procedure: 2-Aminoethanol (13.76 g, 225.3 mmol) was dissolved in CHCl3 (750 ml). To the solution was added dropwise palmitoyl chloride (15.48 g, 56.3 mmol) with stirring under ice cooling. Thereafter, the mixture was stirred at room temperature for 19 hours. Thereafter, the mixture was stirred at room temperature for 19 hours