N-benzylhexan-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:; See reaction.notes.procedure_details.

Procedure: A! 200 ml (1.49 moles) of hexylamine cooled to 5° C. were added with benzyl bromide (42.3 ml, 0.35 mole), and the resultant mixture was stirred for 1 hour at room temperature. The hexylamine in excess was then distilled off under vacuum, and the residue dissolved in 300 ml of ethyl ether and washed with 200 ml of 0.5N sodium hydroxide. The ether phase was anhydrified over sodium sulfate and evaporated to dryness thus yielding 75.5 g of a crude which, by distillation under vacuum, gave 59 g (yield: 89%) of N-benzyl-N-hexylamine (b.p.--90°-95° C./0.6 mmHg). The hexylamine in excess was then distilled off under vacuum the residue dissolved in 300 ml of ethyl ether washed with 200 ml of 0.5N sodium hydroxide evaporated to dryness thus yielding 75.5 g of a crude which by distillation under vacuum

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

Procedure: (4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)acetic acid (50 mg, 0.166 mmol) was dissolved in DCM (2 ml), N-hexylbenzylamine (38.2 mg, 0.2 mmol) was added, then EDC (38.3 mg, 0.2 mmol) was added and then DMAP (24.4 mg, 0.2 mmol) was added. The mixture was stirred at room temperature overnight. 1% HCl (1 ml) and water (1 ml) were added into the mixture. The two phases were separated by using a Whatman Filter Tube. The obtained organic solution was evaporated in vacuum and the oil product (71 mg) was left. It was then used directly in next step. The two phases were separated Filter Tube The obtained organic solution was evaporated in vacuum the oil product (71 mg) was left

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

Procedure: N-hexylbenzylamine (0.6 g, 3.136 mmol) and 3-(4-hydroxyphenyl)propionic acid (0.52 g 3.136 mmol) were mixed in DMF (10 ml) and the mixture was cooled. HOBT (0.424 g, 3.136 mmol) and the TBTU (1 g, 3.136 mmol) reagent were added followed by DIPEA (1.216 g, 9.409 mmol). The mixture was stirred at room temperature overnight and then evaporated. The resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.). The aqueous portion was extracted with ethyl acetate and the combined organic extracts dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using ethyl acetate/heptane (10:90, then 25:75) as eluant gave 760 mg the desired product, yield 71%. the mixture was cooled evaporated The resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.) The aqueous portion was extracted with ethyl acetate the combined organic extracts dried with magnesium sulphate evaporated

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

Procedure: A! 200 ml (1.49 moles) of hexylamine cooled to 5° C. were added with benzyl bromide (42.3 ml, 0.35 mole), and the resultant mixture was stirred for 1 hour at room temperature. The hexylamine in excess was then distilled off under vacuum, and the residue dissolved in 300 ml of ethyl ether and washed with 200 ml of 0.5N sodium hydroxide. The ether phase was anhydrified over sodium sulfate and evaporated to dryness thus yielding 75.5 g of a crude which, by distillation under vacuum, gave 59 g (yield: 89%) of N-benzyl-N-hexylamine (b.p.--90°-95° C./0.6 mmHg). The hexylamine in excess was then distilled off under vacuum the residue dissolved in 300 ml of ethyl ether washed with 200 ml of 0.5N sodium hydroxide evaporated to dryness thus yielding 75.5 g of a crude which by distillation under vacuum

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

Procedure: A! 200 ml (1.49 moles) of hexylamine cooled to 5° C. were added with benzyl bromide (42.3 ml, 0.35 mole), and the resultant mixture was stirred for 1 hour at room temperature. The hexylamine in excess was then distilled off under vacuum, and the residue dissolved in 300 ml of ethyl ether and washed with 200 ml of 0.5N sodium hydroxide. The ether phase was anhydrified over sodium sulfate and evaporated to dryness thus yielding 75.5 g of a crude which, by distillation under vacuum, gave 59 g (yield: 89%) of N-benzyl-N-hexylamine (b.p.--90°-95° C./0.6 mmHg). The hexylamine in excess was then distilled off under vacuum the residue dissolved in 300 ml of ethyl ether washed with 200 ml of 0.5N sodium hydroxide evaporated to dryness thus yielding 75.5 g of a crude which by distillation under vacuum

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

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

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