4-[(3-cyclopentyloxy-4-methoxyphenyl)methyl]imidazolidin-2-one

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of 22.22 g (100 mmoles) of the product obtained in Example 3, step (a) in 220 ml of dimethylsulphoxide, 27 g of powdered anhydrous potassium carbonate are added and the suspension is stirred at 60° C. for 30 minutes, then 12.9 ml (120 mmoles) of cyclopentyl bromide are portionwise added during 60 minutes while the temperature is kept at 60° C. The suspension is further stirred at 60° C. for 20 hours, then cooled to 25° C. and poured into 800 ml of water. The aqueous emulsion is extracted four times with 400 ml of chloroform. The collected organic phases are washed twice with 50 ml of 1 N sodium hydroxide solution, dried over anhydrous magnesium sulphate and evaporated in vacuo. To the oily residue 200 ml of benzene are added and the evaporation is repeated. The residue is triturated with 150 ml of ether and the crystals obtained are filtered after 30 minutes and washed with 50 ml of ether to give 21.30 g (73.4%) of the title compound, m.p. 104°-107° C. After recrystallization from acetone this melting point rises to 115°-116° C. On the basis of its physical properties, this product is identical with the compound obtained in Example 2, step (d). is kept at 60° C The suspension is further stirred at 60° C. for 20 hours cooled to 25° C. The aqueous emulsion is extracted four times with 400 ml of chloroform The collected organic phases are washed twice with 50 ml of 1 N sodium hydroxide solution dried over anhydrous magnesium sulphate evaporated in vacuo To the oily residue 200 ml of benzene are added the evaporation The residue is triturated with 150 ml of ether the crystals obtained are filtered after 30 minutes washed with 50 ml of ether