N-ethylheptan-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:

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

Procedure: In a manner similar to Preparation 4, react ethyl(heptyl)amine with succinic anhydride to obtain the title compound. In a manner similar to Preparation 4

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

Procedure: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and N-ethyl-N-heptylamine as starting materials to give the aimed compound.

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

Procedure: A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170. After 18 hours the reaction mixture is concentrated under reduced pressure The alkaline mixture is extracted with Et2O extracted with CH2Cl2 The CH2Cl2 extracts are concentrated the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

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

Procedure: A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170. After 18 hours the reaction mixture is concentrated under reduced pressure The alkaline mixture is extracted with Et2O extracted with CH2Cl2 The CH2Cl2 extracts are concentrated the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

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

Procedure: A mixture of p-nitrophenylacetic acid (7.14 g, 0.0394 mol), ethylheptylamine (5.64 g, 0.0394 mol) and 1-hydroxybenzotriazole (6.0 g, 0.044 mol) in 35 ml of dimethylformamide (DMF), under nitrogen, is cooled in an ice bath. The mixture is then treated with the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (7.68 g, 0.04 mol) in portions over 15 min. The mixture is stirred in the cold for 1 hr and at room temperature overnight. The mixture is diluted with 400 ml of ethyl acetate and washed twice with saturated NaHCO3. (Each wash is back extracted with ethyl acetate.) The pooled organic extract is washed sequentially with water (50 ml), 1N KHSO4 solution (3×50 ml), water (50 ml) and finally brine (50 ml). It is dried (Na2SO4) and concentrated in vacuo to yield the title compound. This residue is treated with Et2O-pentane, a solid filtered off and the filtrate concentrated in vacuo. The residue is chromatographed over 1400 ml of silica gel with 25% EtOAc-SSB with 42 ml fractions being collected. Fractions at approximately 70-104 yield the title compound as an oil. under nitrogen, is cooled in an ice bath at room temperature overnight washed twice with saturated NaHCO3 (Each wash is back extracted with ethyl acetate ) The pooled organic extract is washed sequentially with water (50 ml), 1N KHSO4 solution (3×50 ml), water (50 ml) and finally brine (50 ml) It is dried (Na2SO4) concentrated in vacuo

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 4-[(methylsulfonyl)amino]-γ-oxobenzenebutanoic acid as prepared in Preparation 2 (12.0 g, 0.044 mol) in DMF (100 ml) under N2 is cooled in an ice bath to 5° C. and treated with 1-hydroxybenzotriazole (5.94 g, 0.044 mol) and N,N'-dicyclohexylcarbodiimide (9.08 g, 0.044 mol). After 1 hour, ethylheptylamine (6.3 g, 0.044 mol) is added; after an additional 30 minutes the ice bath is removed and the mixture is kept at ambient temperature for 18 hours. The reaction mixture is filtered over a Celite filter aid and the filtrate is concentrated under vacuum. The resulting material is dissolved in CH2Cl2 ; washed with dilute HCl, NaHCO3 and brine; dried (Na2SO4) and concentrated. The residue is chromatographed over silica gel (1.25 kg) with 5% MeOH:1% NH4OH:CH2Cl2. The N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide thus obtained is crystallized from EtOAc:SSB to yield 10.77 g, mp 100°-102° C. and 2.32 g, mp 99°-101° C. The analytical sample has a mp 102°-103° C. after an additional 30 minutes the ice bath is removed the mixture is kept at ambient temperature for 18 hours The reaction mixture is filtered over a Celite filter aid the filtrate is concentrated under vacuum The resulting material is dissolved in CH2Cl2 washed with dilute HCl, NaHCO3 and brine dried (Na2SO4) concentrated The residue is chromatographed over silica gel (1.25 kg) with 5% MeOH