2-methyl-2-phenoxypropanoyl chloride

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

Procedure: 2-Methyl-2-phenoxypropionic acid (34 mg, 0.189 mmol) was made into acid chloride in a conventional manner. By using 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (30 mg, 0.095 mmol) obtained in Example 1, (3), and 2-methyl-2-phenoxypropionic acid chloride mentioned above, the title compound (46 mg, yield 100%) was obtained in the same manner as that of Example 1.

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

Procedure: 2-Methyl-2-phenoxypropionic acid (34 mg, 0.189 mmol) was made into acid chloride in a conventional manner. By using 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (30 mg, 0.095 mmol) obtained in Example 1, (3), and 2-methyl-2-phenoxypropionic acid chloride mentioned above, the title compound (46 mg, yield 100%) was obtained in the same manner as that of Example 1.

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

Procedure: To a solution of 17.2 g of anhydrous piperazine in 50 ml of EtOH 95% and 22 ml of H2O, 3.37 g of HBr 48% are dropped in about 10' and thereafter, in about 40' and at room temperature, a solution of 9.93 g of 2-phenoxy-2-methylpropionyl chloride (prepared according to: Bull. Soc. Chim. Fr. 1956, 776-783) in 70 ml of THF. The suspension is stirred 2 h at the same temperature and 3 h under reflux, diluted with 130 ml of THF, cooled, and the piperazine salts precipitated are filtered away. The filtered is evaporated to dryness, the residue is resuspended with 120 ml of H2O and 35 ml HCl 2N and extracted with Et2O; the aqueous phase is treated with 40 ml NaOH conc. and extracted with Et2O (4×50 ml). The ethere-phase, dried, is treated with HCl in Et2 O about 3N and the precipitate is collected by filtration and crystallized from EtOH giving 5.98 g (42%) of the wanted compound; m.p.: 236°-238° C. under reflux cooled the piperazine salts precipitated are filtered away The filtered is evaporated to dryness extracted with Et2O the aqueous phase is treated with 40 ml NaOH conc. extracted with Et2O (4×50 ml) The ethere-phase, dried is treated with HCl in Et2 O about 3N the precipitate is collected by filtration crystallized from EtOH giving 5.98 g (42%) of the wanted compound

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

Procedure: A solution of 0.01 mol of 2-phenoxyisobutyric acid chloride (obtained by reaction of thionyl chloride with 2-phenoxyisobutyric acid) in 100 ml of methylene chloride is introduced into an Erlenmeyer flask containing a solution of 0.01 mol of 1-benzylpiperazine in 100 ml of methylene chloride. The mixture is stirred for 5 hours at room temperature, filtered and evaporated to dryness. The residue is taken up in water, basified and extracted with chloroform. The organic phases are combined, dried and evaporated. filtered evaporated to dryness extracted with chloroform dried evaporated

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

Procedure: A solution of 0.01 mol of 2-phenoxyisobutyric acid chloride (obtained by reaction of thionyl chloride with 2-phenoxyisobutyric acid) in 100 ml of methylene chloride is introduced into an Erlenmeyer flask containing a solution of 0.01 mol of 1-benzylpiperazine in 100 ml of methylene chloride. The mixture is stirred for 5 hours at room temperature, filtered and evaporated to dryness. The residue is taken up in water, basified and extracted with chloroform. The organic phases are combined, dried and evaporated. filtered evaporated to dryness extracted with chloroform dried evaporated

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

Procedure: 2-Methyl-2-phenoxypropionic acid (34 mg, 0.189 mmol) was made into acid chloride in a conventional manner. By using 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (30 mg, 0.095 mmol) obtained in Example 1, (3), and 2-methyl-2-phenoxypropionic acid chloride mentioned above, the title compound (46 mg, yield 100%) was obtained in the same manner as that of Example 1.

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

Procedure: To a solution of 17.2 g of anhydrous piperazine in 50 ml of EtOH 95% and 22 ml of H2O, 3.37 g of HBr 48% are dropped in about 10' and thereafter, in about 40' and at room temperature, a solution of 9.93 g of 2-phenoxy-2-methylpropionyl chloride (prepared according to: Bull. Soc. Chim. Fr. 1956, 776-783) in 70 ml of THF. The suspension is stirred 2 h at the same temperature and 3 h under reflux, diluted with 130 ml of THF, cooled, and the piperazine salts precipitated are filtered away. The filtered is evaporated to dryness, the residue is resuspended with 120 ml of H2O and 35 ml HCl 2N and extracted with Et2O; the aqueous phase is treated with 40 ml NaOH conc. and extracted with Et2O (4×50 ml). The ethere-phase, dried, is treated with HCl in Et2 O about 3N and the precipitate is collected by filtration and crystallized from EtOH giving 5.98 g (42%) of the wanted compound; m.p.: 236°-238° C. under reflux cooled the piperazine salts precipitated are filtered away The filtered is evaporated to dryness extracted with Et2O the aqueous phase is treated with 40 ml NaOH conc. extracted with Et2O (4×50 ml) The ethere-phase, dried is treated with HCl in Et2 O about 3N the precipitate is collected by filtration crystallized from EtOH giving 5.98 g (42%) of the wanted compound