1-(chloromethyl)-4-(2-phenylethyl)benzene

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

Procedure: Under argon, 500 mg (1.07 mmol) of ethyl 5-{(5-ethoxy-5-oxopentyl)[2-(2-hydroxyphenyl)-ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate, 246 mg (1.07 mmol) of 1-(chloromethyl)-4-(2-phenylethyl)benzene and 295 mg (2.13 mmol) of potassium carbonate in 5 ml of DMF were heated to 80° C. and stirred at this temperature for 6 hours. After cooling, water and ethyl acetate were added to the reaction mixture and the phases were then separated. The organic phase was washed twice with water and once with saturated sodium chloride solution and then concentrated to dryness. This gave 760 mg (1.01 mmol, content 88%, 94% of theory) of the target compound. After cooling the phases were then separated The organic phase was washed twice with water and once with saturated sodium chloride solution concentrated to dryness

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

Procedure: 460 mg (2 mmol) of 1-(chloromethyl)-4-(2-phenylethyl)benzene [preparation according to M. Carrara et al., Arzneim. Forsch. 47 (7), 803-809 (1997)] and 414 mg (3 mmol) of anhydrous potassium carbonate are added to a solution of 411 mg (1 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 10 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then evaporated to dryness. The residue is taken up in ethyl acetate, washed with water and with saturated sodium chloride solution and dried over sodium sulphate. After filtration, the organic phase is evaporated and the resulting crude product is purified by preparative HPLC. 431 mg (0.7 mmol, 65% yield) of a solid are obtained. the mixture is heated under reflux for 12 hours The mixture is then evaporated to dryness washed with water and with saturated sodium chloride solution dried over sodium sulphate After filtration the organic phase is evaporated the resulting crude product is purified by preparative HPLC

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

Procedure: Under argon, 500 mg (1.07 mmol) of ethyl 5-{(5-ethoxy-5-oxopentyl)[2-(2-hydroxyphenyl)-ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate, 246 mg (1.07 mmol) of 1-(chloromethyl)-4-(2-phenylethyl)benzene and 295 mg (2.13 mmol) of potassium carbonate in 5 ml of DMF were heated to 80° C. and stirred at this temperature for 6 hours. After cooling, water and ethyl acetate were added to the reaction mixture and the phases were then separated. The organic phase was washed twice with water and once with saturated sodium chloride solution and then concentrated to dryness. This gave 760 mg (1.01 mmol, content 88%, 94% of theory) of the target compound. After cooling the phases were then separated The organic phase was washed twice with water and once with saturated sodium chloride solution concentrated to dryness