1-benzyl-1-phenylhydrazine;hydrochloride

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(6-methoxy-naphthalen-2-yl)heptan-1-one (0.176 kg, 0.651 moles) was dissolved in anhydrous ethanol (1.56 L), 1-benzyl-1-phenylhydrazine hydrochloride (BPH, 0.168 kg, 0.716 moles) was added, a 37% aqueous solution of hydrochloric acid (1.2 g, 12.2 mmoles) was added, and the reaction mixture was heated under reflux for 7 hours. Two portions of BPH (8.4 g, 71.6 mmoles each) were added to the mixture at one hour intervals at 70° C. The temperature of the mixture returned to the reflux temperature after the first BPH addition. Heating was terminated, the reaction mixture was diluted with heptane (1.65 L) followed by water (0.62 kg), and the mixture was stirred for 30 minutes while maintaining the temperature at 45° C. The addition of heptane resulted in the precipitation of solids from the homogeneous organic phase, while the addition of water brought the mixture to a biphasic state with layers in an approximate ratio of 1:1. The bottom layer was drained (pH 1) and the upper layer was washed with water (0.26 kg) while stirring the mixture for 30 minutes. The bottom layer was again drained (pH 3) and the upper layer was cooled to 12° C. in the reactor. All operations subsequent to the quenching step were conducted at 45° C. to prevent premature product crystallization. About 10 grams of the chilled solution were withdrawn from the reactor, subjected to low-temperature crystallization, and returned to the chilled solution as a seeding suspension. The mixture was kept at 12° C. for 30 minutes, cooled to −10° C. over two hours, and stirred at that temperature for 30 minutes. The suspension was filtered, the solids were dried in a nitrogen stream on a filter for 30 minutes, and the solids were vacuumed at 50° C./50 mm Hg to yield 221 g (78%) of the title compound as light-yellow prills with 99.45% ar. HPLC purity. the reaction mixture was heated under reflux for 7 hours Heating was terminated the reaction mixture was diluted with heptane (1.65 L) The addition of heptane resulted in the precipitation of solids from the homogeneous organic phase, while the addition of water the upper layer was washed with water (0.26 kg) while stirring the mixture for 30 minutes the upper layer was cooled to 12° C. in the reactor were conducted at 45° C. product crystallization About 10 grams of the chilled solution were withdrawn from the reactor subjected to low-temperature crystallization The mixture was kept at 12° C. for 30 minutes cooled to −10° C. over two hours stirred at that temperature for 30 minutes The suspension was filtered the solids were dried in a nitrogen stream on a filter for 30 minutes were vacuumed at 50° C.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Generally, a suspension of equimolar amounts of 1-(6-methoxynaphthalen-2-yl)heptan-1-one and N-benzyl-N-phenylhydrazine hydrochloride (BPH) in ethanol is heated under reflux for five hours. Two portions of 0.1 equivalent of BPH in ethanol are added to the suspension at one hour intervals. Alternatively, the solution of BPH in ethanol is added to reaction mixture continuously. The resulting mixture is refluxed for an hour, diluted with heptane, and treated with water at 45° C. The organic and aqueous phases are separated, and the organic phase is washed with water and cooled to 10° C. to initiate crystallization. Upon cooling to −15° C., 80%-85% of crystalline 1-benzyl-2-(6-methoxy-naphthalen-2-yl)-3-pentyl-1H-indole is obtained. is heated under reflux for five hours The resulting mixture is refluxed for an hour The organic and aqueous phases are separated the organic phase is washed with water crystallization Upon cooling to −15° C.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Generally, a suspension of equimolar amounts of 1-(6-methoxynaphthalen-2-yl)heptan-1-one and N-benzyl-N-phenylhydrazine hydrochloride (BPH) in ethanol is heated under reflux for five hours. Two portions of 0.1 equivalent of BPH in ethanol are added to the suspension at one hour intervals. Alternatively, the solution of BPH in ethanol is added to reaction mixture continuously. The resulting mixture is refluxed for an hour, diluted with heptane, and treated with water at 45° C. The organic and aqueous phases are separated, and the organic phase is washed with water and cooled to 10° C. to initiate crystallization. Upon cooling to −15° C., 80%-85% of crystalline 1-benzyl-2-(6-methoxy-naphthalen-2-yl)-3-pentyl-1H-indole is obtained. is heated under reflux for five hours The resulting mixture is refluxed for an hour The organic and aqueous phases are separated the organic phase is washed with water crystallization Upon cooling to −15° C.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Generally, a suspension of equimolar amounts of 1-(6-methoxynaphthalen-2-yl)heptan-1-one and N-benzyl-N-phenylhydrazine hydrochloride (BPH) in ethanol is heated under reflux for five hours. Two portions of 0.1 equivalent of BPH in ethanol are added to the suspension at one hour intervals. Alternatively, the solution of BPH in ethanol is added to reaction mixture continuously. The resulting mixture is refluxed for an hour, diluted with heptane, and treated with water at 45° C. The organic and aqueous phases are separated, and the organic phase is washed with water and cooled to 10° C. to initiate crystallization. Upon cooling to −15° C., 80%-85% of crystalline 1-benzyl-2-(6-methoxy-naphthalen-2-yl)-3-pentyl-1H-indole is obtained. is heated under reflux for five hours The resulting mixture is refluxed for an hour The organic and aqueous phases are separated the organic phase is washed with water crystallization Upon cooling to −15° C.