1-phenylpentan-2-one

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

Procedure: As in Example 130, 1-phenylpentanone (50 g) was reacted with diethyl succinate (80.5 g) in t-butanol at 60° C. for 6 hours in the presence of potassium t-butoxide (38 g). The normal work up furnished 81 g of a mixture of the isomeric 3-(ethoxycarbonyl)-3-octenoic acids as an oil. The acids (79.4 g) were cyclized as before by refluxing in acetic anhydride (500 mL) containing sodium acetate (22.5 g) for 9 hours. After work up, the crude product was passed through a short column of silica gel (650 g) made up in dichloromethane-hexane (2:1) to give 60 g of 4-acetoxy-1-butyl-2-naphthalenecarboxylic acid ethyl ester as an oil.

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

Procedure: 11.0 g (0.068 mole) of benzyl-propyl-ketone are dissolved in 110 ml of benzene, whereupon 8.0 g (0.135 mole) of n-propyl-amine and 22.6 g (0.2 mole) of anhydrous calcium chloride are added to the solution. The reaction mixture is stirred at 40°-50° C. for 6 hours, then filtered and evaporated. The crude ketimine thus obtained is dissolved in 120 ml of methanol, whereupon 6.4 g (0.17 mole) of sodium borohydride are added. The reaction mixture is allowed to stand, whereupon it is poured into 500 ml of water and extracted five times with 100 ml of benzene each. The benzene solution is dried and evaporated. The crude N-propyl-1-phenyl-2-pentylamine thus obtained is purified by distillation in vacuo. B.p.: 112°-120° C./7 Hgmm, n20D =1.5030. are added to the solution filtered evaporated The crude ketimine thus obtained are added extracted five times with 100 ml of benzene each The benzene solution is dried evaporated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-phenylpentan-2-one (5.00 g, 30.8 mmol) in dry DMF (80.0 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (6.16 mL, 46.2 mmol). The resulting mixture was heated at 90° C. After 16 h, the reaction mixture was quenched with water, extracted with EtOAc (3×) and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give a yellow oil. This yellow oil was purified by silica gel flash chromatography to give the title compound as a yellow oil (3.51 g). 1H NMR (400 MHz, CDCl3) δ ppm 0.76-0.83 (m, 3H), 0.83-0.89 (m, 2H), 2.11-2.19 (m, 2H), 2.62-2.71 (m, 6H), 7.15-7.42 (m, 5H), 7.61 (s, 1H). the reaction mixture was quenched with water extracted with EtOAc (3×) washed with brine The combined organics were dried over MgSO4 filtered concentrated to give a yellow oil This yellow oil was purified by silica gel flash chromatography

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

Procedure: 11.0 g (0.068 mole) of benzyl-propyl-ketone are dissolved in 110 ml of benzene, whereupon 8.0 g (0.135 mole) of n-propylamine and 22.6 g (0.2 mole) of anhydrous calcium chloride are added to the solution. The reaction mixture is stirred at 40°-50° C. for 6 hours, then filtered and evaporated. The crude ketimine thus obtained is dissolved in 120 ml of methanol, whereupon 6.4 g (0.17 mole) of sodium borohydride are added. The reaction mixture is allowed to stand, whereupon it is poured into 500 ml of water and extracted five times with 100 of benzene each. The benzene solution is dried and evaporated. The crude N-propyl-1-phenyl-2-pentylamine thus obtained is purified by distillation in vacuo. B.p.: 112°-120° C./7 Hgmm, n20D =1.5030. are added to the solution filtered evaporated The crude ketimine thus obtained are added extracted five times with 100 of benzene each The benzene solution is dried evaporated