(4-benzylphenyl)methanol

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

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

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

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

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methanesulfonyl chloride (4.2 mg, 0.037 mmol) in CHCl3 (1.0 mL) and (piperidinomethyl)polystyrene (54 mg, 2.7 mmol base/g resin) were added to a solution of 4-(benzyl)benzyl alcohol (8.7 mg, 0.044 mmol) in CHCl3 (1.0 mL). The reaction mixture was stirred at 25° C. for 15 h. A solution of 4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (15.1 mg, 0.044 mmol) in CH3CN (1.0 mL) and KI (2 mg) were added to the reaction mixture and the mixture was stirred at 65° C. for 5 h. Phenyl isocyanate (5.2 mg) was added to the cooled reaction mixture and the mixture was stirred at 25° C. for 1 h. The reaction mixture was loaded onto Varian™ SCX column and washed with CH3OH (20 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford 1-(4-benzylbenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (compound No. 926) as a pale yellow oil (5.6 mg, 29): The purity was determined by RPLC/MS (94%); ESI/MS m/e 524.1 (M++H, C30H32F3N3O2). the mixture was stirred at 65° C. for 5 h the mixture was stirred at 25° C. for 1 h washed with CH3OH (20 mL) Product was eluted off concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methanesulfonyl chloride (4.2 mg, 0.037 mmol) in CHCl3 (1.0 mL) and (piperidinomethyl)polystyrene (54 mg, 2.7 mmol base/g resin) were added to a solution of 4-(benzyl)benzyl alcohol (8.7 mg, 0.044 mmol) in CHCl3 (1.0 mL). The reaction mixture was stirred at 25° C. for 15 h. A solution of 4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (15.1 mg, 0.044 mmol) in CH3CN (1.0 mL) and KI (2 mg) were added to the reaction mixture and the mixture was stirred at 65° C. for 5 h. Phenyl isocyanate (5.2 mg) was added to the cooled reaction mixture and the mixture was stirred at 25° C. for 1 h. The reaction mixture was loaded onto Varian™ SCX column and washed with CH3OH (20 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford 1-(4-benzylbenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (compound No. 926) as a pale yellow oil (5.6 mg, 29): The purity was determined by RPLC/MS (94%); ESI/MS m/e 524.1 (M++H, C30H32F3N3O2). the mixture was stirred at 65° C. for 5 h the mixture was stirred at 25° C. for 1 h washed with CH3OH (20 mL) Product was eluted off concentrated

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

Procedure: 4-Benzylbenzyl bromide was prepared from 20 g. of 4-benzylbenzyl alcohol [Maquin et al., Compt. rend. 234, 629-31, 1952] and hydrogen bromide according to the procedure of Example 1, part (e). An oil (25.7 g.) was obtained which was used directly in the next reaction. An oil (25.7 g.) was obtained which was used directly in the next reaction

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

Procedure: 4-Benzylbenzyl bromide was prepared from 20 g. of 4-benzylbenzyl alcohol [Maquin et al., Compt. rend. 234, 629-31, 1952] and hydrogen bromide according to the procedure of Example 1, part (e). An oil (25.7 g.) was obtained which was used directly in the next reaction. An oil (25.7 g.) was obtained which was used directly in the next reaction

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-benzylbenzyl alcohol (181.47 g) was dissolved into chloroform (100 ml), and thionyl chloride (66.8 ml) was added with stirring at a 0° C. After stirring at 0° C. for 4 hours, reaction mixture was concentrated under reduced pressure to give the title compound (198.34 g). This product was used in the subsequent procedure without purification. was added After stirring at 0° C. for 4 hours reaction mixture was concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-benzylbenzyl alcohol (181.47 g) was dissolved into chloroform (100 ml), and thionyl chloride (66.8 ml) was added with stirring at a 0° C. After stirring at 0° C. for 4 hours, reaction mixture was concentrated under reduced pressure to give the title compound (198.34 g). This product was used in the subsequent procedure without purification. was added After stirring at 0° C. for 4 hours reaction mixture was concentrated under reduced pressure

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

Procedure: By using ethyl 4-benzylbenzoate (232.55 g), lithium aluminium hydride (23.00 g) and ether (1.3 l), there was prepared the title compound (181.47 g).