3-(4-methoxyphenyl)propanoyl chloride

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

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

Procedure: By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and 3-(4-methoxyphenyl)propionyl chloride, the title compound was synthesized according to Example 1b. Yield: 72%. Melting point: 188-191° C. (Ethyl acetate-hexane).

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

Procedure: By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and 3-(4-methoxyphenyl)propionyl chloride, the title compound was synthesized according to Example 1b. Yield: 72%. Melting point: 188-191° C. (Ethyl acetate-hexane).

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

Procedure: By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and 3-(4-methoxyphenyl)propionyl chloride, the title compound was synthesized according to Example 1b. Yield: 72%. Melting point: 188-191° C. (Ethyl acetate-hexane)

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

Procedure: To a suspension of barbituric Acid (6.4 g) in 48 ml of pyridine are added dropwise 11 g of 3-(4-Methoxyphenyl)propionyl chloride and the mixture is stirred at room temperature for 18 hours. The reaction mixture is then poured into ice and acidified to pH=1 by adding 6 N hydrochloric acid. A solid precipitates, which is filtered and resuspended in methanol. The suspension is kept under stirring for 15 minutes, then the solid is recovered by filtration to give 12.2 g of the product m.p. 248-250° C. The reaction mixture is then poured into ice A solid precipitates which is filtered under stirring for 15 minutes the solid is recovered by filtration

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 3-(4-Methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65° C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil. The solvent is evaporated off under reduced pressure the residue is redissolved in toluene concentrated to dryness

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 3-(4-Methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65° C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil. The solvent is evaporated off under reduced pressure the residue is redissolved in toluene concentrated to dryness

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

Procedure: To a stirred mixture of 1.0 g (3.5 mmol) of 2-amino-6-(3-(3-pyridyl)allyl)-4,5,7,8-tetrahydro-6H- thiazolo[5,4-d]azepine and 0.53 ml (3.8 mmol) of triethylamine in 40 ml of anhydrous chloroform, there is added dropwise at ambient temperature a solution of 3- (4-methoxy-phenyl)-propionyl chloride (bp: 150° C./15 torr) in 7 ml of chloroform. The mixture is stirred for 3 hours at 60°-70° C., cooled and extracted with water. The dried and filtered chloroform solution is evaporated down in vacuo and the evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1). Yield: 0.74 g (47% of theory), Melting point: 168°-170° C. (ether). cooled extracted with water The dried filtered chloroform solution is evaporated down in vacuo the evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1)

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

Procedure: 15.1 g (0.09 mol) of 6-oxo-2-amino-tetrahydrobenzothiazole and 20.5 g (0.1-mol) of 4-methoxyphenylpropionyl chloride are refluxed for 2 hours in 450 ml of tetrahydrofuran and 0.1 mol of triethylamine, subsequently poured onto ice and extracted with ethyl acetate. After drying, 2-(4-methoxyphenylpropionyl)amino-6-oxo-tetrahydrobenzothiazole (17.5 g) crystallises out on concentrating, and, is dissolved in methanol and is reductively aminated, without further purification, in an autoclave using propylamine (Raney nickel, 5 bar, 60° C.). After filtering off the catalyst under suction, the solvent is removed by distillation. The residue crystallises from i-propyl ether. Yield: 12.5 g (63% of theory) extracted with ethyl acetate After drying 2-(4-methoxyphenylpropionyl)amino-6-oxo-tetrahydrobenzothiazole (17.5 g) crystallises out on concentrating is dissolved in methanol is reductively aminated, without further purification, in an autoclave propylamine (Raney nickel, 5 bar, 60° C.) After filtering off the catalyst under suction the solvent is removed by distillation The residue crystallises from i-propyl ether

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

Procedure: 15.1 g (0.09 mol) of 6-oxo-2-amino-tetrahydrobenzothiazole and 20.5 g (0.1-mol) of 4-methoxyphenylpropionyl chloride are refluxed for 2 hours in 450 ml of tetrahydrofuran and 0.1 mol of triethylamine, subsequently poured onto ice and extracted with ethyl acetate. After drying, 2-(4-methoxyphenylpropionyl)amino-6-oxo-tetrahydrobenzothiazole (17.5 g) crystallises out on concentrating, and, is dissolved in methanol and is reductively aminated, without further purification, in an autoclave using propylamine (Raney nickel, 5 bar, 60° C.). After filtering off the catalyst under suction, the solvent is removed by distillation. The residue crystallises from i-propyl ether. Yield: 12.5 g (63% of theory) extracted with ethyl acetate After drying 2-(4-methoxyphenylpropionyl)amino-6-oxo-tetrahydrobenzothiazole (17.5 g) crystallises out on concentrating is dissolved in methanol is reductively aminated, without further purification, in an autoclave propylamine (Raney nickel, 5 bar, 60° C.) After filtering off the catalyst under suction the solvent is removed by distillation The residue crystallises from i-propyl ether

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

Procedure: A solution of 13.73 g. of benzocaine and 11.56 ml. of triethylamine in 100 ml. of ether is slowly added to a stirred solution of 15 g. of p-methoxyhydrocinnamoyl chloride in 100 ml. of ether. The mixture is stirred overnight, 250 ml. of dichloromethane are added, and the mixture is extracted with 200 ml. of water, then 200 ml. of 10% hydrochloric acid, dried over magnesium sulfate, and evaporated to yield a solid. This solid is crystallized from 200 ml. of toluene, giving 21.4 g. of the desired product as white crystals, m.p. 134°-135.5° C. the mixture is extracted with 200 ml of 10% hydrochloric acid, dried over magnesium sulfate evaporated to yield a solid This solid is crystallized from 200 ml of toluene, giving 21.4 g

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

Procedure: By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and 3-(4-methoxyphenyl)propionyl chloride, the title compound was synthesized according to Example 1b. Yield: 72%. Melting point: 188-191° C. (Ethyl acetate-hexane).