Phenol, 4-[2-[(3,3-diphenylpropyl)amino]propyl]-

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

Procedure: The mixture of 18.3 g of 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 100 ml of dimethylsulfoxide and 5.29 ml of 10 N-aqueous sodium hydroxide is stirred at room temperature for one hour, combined with 9.66 g of 4-t-butylbenzyl chloride and stirred 18 hours longer. It is poured into 1,000 ml of water, extracted twice with 500 ml of methylene chloride, the extract dried and evaporated at about 60°. The residue is taken up in isopropanol, the solution acidified with 5% isopropanolic maleic acid, the precipitate collected and recrystallized from isopropanol-diethyl ether, to yield the 1-[4-(4-t-butylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane maleate melting at 132°-134°. stirred 18 hours longer extracted twice with 500 ml of methylene chloride the extract dried evaporated at about 60° the precipitate collected recrystallized from isopropanol-diethyl ether

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

Procedure: The mixture of 18.3 g of 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 100 ml of dimethylsulfoxide and 5.29 ml of 10 N-aqueous sodium hydroxide is stirred at room temperature for one hour, combined with 9.66 g of 4-t-butylbenzyl chloride and stirred 18 hours longer. It is poured into 1,000 ml of water, extracted twice with 500 ml of methylene chloride, the extract dried and evaporated at about 60°. The residue is taken up in isopropanol, the solution acidified with 5% isopropanolic maleic acid, the precipitate collected and recrystallized from isopropanol-diethyl ether, to yield the 1-[4-(4-t-butylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane maleate melting at 132°-134°. stirred 18 hours longer extracted twice with 500 ml of methylene chloride the extract dried evaporated at about 60° the precipitate collected recrystallized from isopropanol-diethyl ether

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

Procedure: The mixture of 10.0 g 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 50 ml of dimethylsulfoxide and 2.4 g of sodium hydroxide in 10 ml of water is stirred at 60° for a half hour, whereupon 5.9 g of 2-cyanobenzyl bromide are added and the whole is stirred at room temperature for 20 hours. The mixture is diluted with water, extracted with ethyl acetate & the extract dried and evaporated. The residue is dissolved in the minimum amount of isopropanol, the solution neutralized with isopropanolic oxalic acid and the crude precipitate chromatographed on silica gel, using chloroform eluate, followed by chloroform-methanol (1:1). The initial fraction yields the 1-[4-(2-cyanobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 2220 and 907 cm-1, and the second fraction the 1-[4-(2-carbamoylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 1655 and 1450 cm-1. The latter amide is taken up in aqueous ammonia, the mixture extracted with ethyl acetate & the extract dried and acidified with ethereal hydrogen chloride, to yield the corresponding hydrochloride melting at about 100° with decomposition. are added extracted with ethyl acetate the extract dried evaporated The residue is dissolved in the minimum amount of isopropanol the crude precipitate chromatographed on silica gel

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

Procedure: The mixture of 10.0 g 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 50 ml of dimethylsulfoxide and 2.4 g of sodium hydroxide in 10 ml of water is stirred at 60° for a half hour, whereupon 5.9 g of 2-cyanobenzyl bromide are added and the whole is stirred at room temperature for 20 hours. The mixture is diluted with water, extracted with ethyl acetate & the extract dried and evaporated. The residue is dissolved in the minimum amount of isopropanol, the solution neutralized with isopropanolic oxalic acid and the crude precipitate chromatographed on silica gel, using chloroform eluate, followed by chloroform-methanol (1:1). The initial fraction yields the 1-[4-(2-cyanobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 2220 and 907 cm-1, and the second fraction the 1-[4-(2-carbamoylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 1655 and 1450 cm-1. The latter amide is taken up in aqueous ammonia, the mixture extracted with ethyl acetate & the extract dried and acidified with ethereal hydrogen chloride, to yield the corresponding hydrochloride melting at about 100° with decomposition. are added extracted with ethyl acetate the extract dried evaporated The residue is dissolved in the minimum amount of isopropanol the crude precipitate chromatographed on silica gel

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

Procedure: The mixture of 21.76 g of dl-1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 6.3 ml of 10 N aqueous sodium hydroxide and 100 ml of dimethylsulphoxide is stirred at 60° for 2 hours, whereupon 8.91 g of 5-methyl-2-pyridylmethyl chloride are added. The whole is stirred at ambient temperature for 24 hours, diluted with 400 ml of water and extracted with methylene chloride. The extract is dried, evaporated, the residual oil taken up in isopropanol and the solution acidified with maleic acid in isopropanol until the pH of 5 is reached, to yield the dl-1-[4-(5-methyl-2-pyridylmethoxy)-phenyl]-2-(3,3-diphenylpropylamino)propane maleate, melting at 155°-157°. are added extracted with methylene chloride The extract is dried evaporated

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

Procedure: The mixture of 21.76 g of dl-1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 6.3 ml of 10 N aqueous sodium hydroxide and 100 ml of dimethylsulphoxide is stirred at 60° for 2 hours, whereupon 8.91 g of 5-methyl-2-pyridylmethyl chloride are added. The whole is stirred at ambient temperature for 24 hours, diluted with 400 ml of water and extracted with methylene chloride. The extract is dried, evaporated, the residual oil taken up in isopropanol and the solution acidified with maleic acid in isopropanol until the pH of 5 is reached, to yield the dl-1-[4-(5-methyl-2-pyridylmethoxy)-phenyl]-2-(3,3-diphenylpropylamino)propane maleate, melting at 155°-157°. are added extracted with methylene chloride The extract is dried evaporated

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

Procedure: The mixture of 18.3 g of 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 100 ml of dimethylsulfoxide and 5.29 ml of 10 N-aqueous sodium hydroxide is stirred at room temperature for one hour, combined with 9.66 g of 4-t-butylbenzyl chloride and stirred 18 hours longer. It is poured into 1,000 ml of water, extracted twice with 500 ml of methylene chloride, the extract dried and evaporated at about 60°. The residue is taken up in isopropanol, the solution acidified with 5% isopropanolic maleic acid, the precipitate collected and recrystallized from isopropanol-diethyl ether, to yield the 1-[4-(4-t-butylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane maleate melting at 132°-134°. stirred 18 hours longer extracted twice with 500 ml of methylene chloride the extract dried evaporated at about 60° the precipitate collected recrystallized from isopropanol-diethyl ether

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

Procedure: The mixture of 10.0 g 1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 50 ml of dimethylsulfoxide and 2.4 g of sodium hydroxide in 10 ml of water is stirred at 60° for a half hour, whereupon 5.9 g of 2-cyanobenzyl bromide are added and the whole is stirred at room temperature for 20 hours. The mixture is diluted with water, extracted with ethyl acetate & the extract dried and evaporated. The residue is dissolved in the minimum amount of isopropanol, the solution neutralized with isopropanolic oxalic acid and the crude precipitate chromatographed on silica gel, using chloroform eluate, followed by chloroform-methanol (1:1). The initial fraction yields the 1-[4-(2-cyanobenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 2220 and 907 cm-1, and the second fraction the 1-[4-(2-carbamoylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane, showing I. R. bands at 1655 and 1450 cm-1. The latter amide is taken up in aqueous ammonia, the mixture extracted with ethyl acetate & the extract dried and acidified with ethereal hydrogen chloride, to yield the corresponding hydrochloride melting at about 100° with decomposition. are added extracted with ethyl acetate the extract dried evaporated The residue is dissolved in the minimum amount of isopropanol the crude precipitate chromatographed on silica gel