N-[(4-fluorophenyl)methyl]cyclopentanamine

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

Procedure: 6.75 g (0.05 mol) of phenyl isothiocyanate were rapidly added dropwise to a solution of 9.65 g (0.05 mol) of N-4-fluorobenzyl-N-cyclopentylamine in 80 ml of toluene. The mixture was heated to the boil for 30 minutes, the solvent was distilled off in vacuo, and the residue was recrystallized from isopropanol. 13.8 g of N-4-fluorobenzyl-N-cyclopentyl-N'-phenylthiourea of melting point 135° C. were obtained. The mixture was heated to the boil for 30 minutes the solvent was distilled off in vacuo the residue was recrystallized from isopropanol

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

Procedure: 6.1 g (0.05 mol) of phenyl isocyanate were added dropwise to a solution of 9.65 g (0.05 mol) of N-4-fluorobenzyl-N-cyclopentylamine in 80 ml of anhydrous methylene chloride, while cooling with ice and stirring. The mixture was stirred for 30 minutes at room temperature and for 30 minutes at 40° C., the solvent was stripped off in vacuo, and the residue was recrystallized from acetonitrile. 14.1 g of N-4-fluorobenzyl-N-cyclopentyl-N'-phenylurea of melting point 120° to 121° C. were obtained. while cooling with ice The mixture was stirred for 30 minutes at room temperature and for 30 minutes at 40° C. the residue was recrystallized from acetonitrile

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

Procedure: 160 ml of methanol are added to 18.2 g of sodium borohydride. 90.7 g of 4-fluorobenzaldehyde-cyclopentylimide are added dropwise at 10°-15° C., while cooling with ice and stirring, and the mixture was then stirred for 1.5 hours at room temperature. 120 ml of H2O and 150 ml of methylene chloride were then added, the methylene chloride phase was separated off, and the aqueous phase was further extracted twice with CH2Cl2. The combined methylene chloride phases were washed with water and dried with Na2SO4, and the solvent was stripped off in vacuo. Distillation of the residue under a medium vacuum gave 85.9 g of N-4-fluorobenzyl-N-cyclopentylamine of boiling point 106° C. 0.25 bar. while cooling with ice the mixture was then stirred for 1.5 hours at room temperature the methylene chloride phase was separated off the aqueous phase was further extracted twice with CH2Cl2 The combined methylene chloride phases were washed with water dried with Na2SO4 Distillation of the residue under a medium vacuum