1-(2-fluorophenyl)piperazine;hydrochloride

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

Procedure: Using 5.3 g (0.02 mol) of 4-benzyloxy-3-methylnaphthol, 2.8 g (0.02 mol) of anhydrous potassium carbonate, 9.3 g (0.10 mol) of chloromethyloxirane, 4.3 g (0.02 mol) of 1-(2-fluorophenyl)piperazine hydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Example 1-A to give 6.2 g of white crystals, m.p. 218-220° C. (decomp.).

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

Procedure: Using 5.3 g (0.02 mol) of 4-benzyloxy-3-methylnaphthol, 2.8 g (0.02 mol) of anhydrous potassium carbonate, 9.3 g (0.10 mol) of chloromethyloxirane, 4.3 g (0.02 mol) of 1-(2-fluorophenyl)piperazine hydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Example 1-A to give 6.2 g of white crystals, m.p. 218-220° C. (decomp.).

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

Procedure: Using 5.3 g (0.02 mol) of 4-benzyloxy-3-methylnaphthol, 2.8 g (0.02 mol) of anhydrous potassium carbonate, 9.3 g (0.10 mol) of chloromethyloxirane, 4.3 g (0.02 mol) of 1-(2-fluorophenyl)piperazine hydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Example 1-A to give 6.2 g of white crystals, m.p. 218-220° C. (decomp.).

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

Procedure: This compound was prepared according to the procedure used in Preparation 1. A mixture of 15.1 g (0.09 mol) of bis(2-chloroethyl)amine hydrochloride, 10.0 g (0.09 mol) of 2-fluoroaniline and 25.0 g of solid potassium carbonate in a total volume of 100 mL of 1-butanol gave an oil as residue. The oil was converted to the hydrochloric acid salt (ethereal HCl) and recrystallized from methanol-ether to give 4.0 g (20%) of white solid, mp 185°-187° C. This compound was prepared used in Preparation 1 gave an oil as residue recrystallized from methanol-ether

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

Procedure: The procedures of Example 6 (1) and (2) were repeated but substituting the 1,2,3,4-tetrahydroisoquinoline hydrochloride employed in Example 6 (1) by 1-(2-fluorophenyl)piperazine hydrochloride. After the completion of the post treatment, the title compound was obtained.

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

Procedure: Following the general procedure of Example 11 and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.294 g) and 1-(2-fluorophenyl)piperazine hydrochloride (Aldrich; 0.366 g) are converted to 0.268 g of the title compound after chromatography on silica gel using methanol/dichloromethane (6/94) and crystallization from ethyl acetate/hexane; mp 107-108° C.; MS m/z 344, 346; IR (mineral oil) 1501, 1221, 752, 1335, 927 cm-1 ; 1H NMR (CDCl3) δ2.76, 3.13, 3.78, 6.95, 7.03, 7.12, 7.52, 8.14.

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

Procedure: Using 5.3 g (0.02 mol) of 4-benzyloxy-3-methylnaphthol, 2.8 g (0.02 mol) of anhydrous potassium carbonate, 9.3 g (0.10 mol) of chloromethyloxirane, 4.3 g (0.02 mol) of 1-(2-fluorophenyl)piperazine hydrochloride and 2.0 g (0.02 mol) of triethylamine, reaction was carried out as in Example 1-A to give 6.2 g of white crystals, m.p. 218-220° C. (decomp.).