1-(2-propan-2-ylphenyl)piperazine

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

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

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

Procedure: 100 mg of the target compound (0.27 mmol, 49.1%) was obtained using 1-(2-isopropylphenyl)piperazine (223 mg, 1.09 mmol), biphenyl-2-carbaldehyde (100 mg, 0.55 mmol) and NaBH(OAc)3 (355 mg, 1.65 mmol) according to the synthesis method of Compound 1.

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

Procedure: A mixture of bis(2-chloroethyl)amine hydrochloride (19.78 g, 0.111 mole) and 200 mL of n-butanol was treated dropwise with 2-isopropylaniline (15.0 g, 0.111 mole) and the resulting mixture was stirred for 48 hr at reflux under an argon atmosphere. After cooling to room temperature, anhydrous sodium carbonate (5.86 g, 0.555 mole) was added and the reaction mixture was stirred for another 24 hr at reflux. The reaction was cooled in ice and a white precipitate was filtered off. This material was mixed thoroughly in methylene chloride and 3N sodium hydroxide until the aqueous layer was basic. The methylene chloride layer was separated, dried over anhydrous potassium carbonate, filtered and evaporated affording 6.82 g of 1-[2-(methylethyl)phenyl]piperazine as an oil. The fumarate acid salt was prepared from isopropanol/methanol and recrystallized from methanol to give a white crystalline solid, mp 188-189° C. (Ho). at reflux under an argon atmosphere the reaction mixture was stirred for another 24 hr at reflux The reaction was cooled in ice a white precipitate was filtered off This material was mixed thoroughly in methylene chloride The methylene chloride layer was separated dried over anhydrous potassium carbonate filtered evaporated

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

Procedure: 100 mg of the target compound (0.27 mmol, 49.1%) was obtained using 1-(2-isopropylphenyl)piperazine (223 mg, 1.09 mmol), biphenyl-2-carbaldehyde (100 mg, 0.55 mmol) and NaBH(OAc)3 (355 mg, 1.65 mmol) according to the synthesis method of Compound 1.

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

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

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

Procedure: Phenyl-N-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)carbamate and 1-(2-isopropylphenyl)piperazine were reacted by the same way with the example 1 to obtain the titled compound.

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

Procedure: Phenyl N-(2-methoxyquinoxalin-3-yl)carbamate and 1-(2-isopropylphenyl)piperazine were reacted by the same way with the example 36 to obtain the titled compound.

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

Procedure: Phenyl N-(5,6-dimethyl-2-methoxypyrazin-3-yl)carbamate and 1-(2-isopropylphenyl)piperazine were reacted by the same way with the example 1 to obtain the titled compound.

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

Procedure: The title compound was prepared in a manner similar to Preparation 1A except that piperazine was coupled to 1-bromo-2-isopropyl-benzene. LRMS (ESI+): 205.4 (M+1)

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

Procedure: A mixture of bis(2-chloroethyl)amine hydrochloride (19.78 g, 0.111 mole) and 200 mL of n-butanol was treated dropwise with 2-isopropylaniline (15.0 g, 0.111 mole) and the resulting mixture was stirred for 48 hr at reflux under an argon atmosphere. After cooling to room temperature, anhydrous sodium carbonate (5.86 g, 0.555 mole) was added and the reaction mixture was stirred for another 24 hr at reflux. The reaction was cooled in ice and a white precipitate was filtered off. This material was mixed thoroughly in methylene chloride and 3N sodium hydroxide until the aqueous layer was basic. The methylene chloride layer was separated, dried over anhydrous potassium carbonate, filtered and evaporated affording 6.82 g of 1-[2-(methylethyl)phenyl]piperazine as an oil. The fumarate acid salt was prepared from isopropanol/methanol and recrystallized from methanol to give a white crystalline solid, mp 188-189° C. (Ho). at reflux under an argon atmosphere the reaction mixture was stirred for another 24 hr at reflux The reaction was cooled in ice a white precipitate was filtered off This material was mixed thoroughly in methylene chloride The methylene chloride layer was separated dried over anhydrous potassium carbonate filtered evaporated