N,N-dimethyl-2-(2-piperazin-1-ylphenoxy)ethanamine

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

Procedure: To a solution of 1-Boc-4(2-hydroxyphenyl)-piperazine (300 mg, 1.08 mmol), 2-dimethylaminoethyl chloride hydrochloride (233 mg, 1.62 mmol), K2CO3 (450 mg, 3.26 mmol), and KI (357 mg, 2.15 mmol) in DMF (10 mL) was added 18-crown-6 (1.42 g, 5.37 mmol). After stirring overnight, water was added and the solution extracted with CH2Cl2 (3×). The combined organic extracts were concentrated to an oil. The oil was loaded onto a 10 g SCX ion exchange column equilibrated with MeOH. The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH. The fractions containing desired product were combined and concentrated to an oil. To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O. After stirring overnight the solution was concentrated to an oil to obtain the final compound. MS: 250.2 (M+1). the solution extracted with CH2Cl2 (3×) The combined organic extracts were concentrated to an oil The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH The fractions containing desired product concentrated to an oil To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O After stirring overnight the solution was concentrated to an oil

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

Procedure: To a solution of 1-Boc-4(2-hydroxyphenyl)-piperazine (300 mg, 1.08 mmol), 2-dimethylaminoethyl chloride hydrochloride (233 mg, 1.62 mmol), K2CO3 (450 mg, 3.26 mmol), and KI (357 mg, 2.15 mmol) in DMF (10 mL) was added 18-crown-6 (1.42 g, 5.37 mmol). After stirring overnight, water was added and the solution extracted with CH2Cl2 (3×). The combined organic extracts were concentrated to an oil. The oil was loaded onto a 10 g SCX ion exchange column equilibrated with MeOH. The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH. The fractions containing desired product were combined and concentrated to an oil. To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O. After stirring overnight the solution was concentrated to an oil to obtain the final compound. MS: 250.2 (M+1). the solution extracted with CH2Cl2 (3×) The combined organic extracts were concentrated to an oil The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH The fractions containing desired product concentrated to an oil To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O After stirring overnight the solution was concentrated to an oil

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

Procedure: To a solution of 1-Boc-4(2-hydroxyphenyl)-piperazine (300 mg, 1.08 mmol), 2-dimethylaminoethyl chloride hydrochloride (233 mg, 1.62 mmol), K2CO3 (450 mg, 3.26 mmol), and KI (357 mg, 2.15 mmol) in DMF (10 mL) was added 18-crown-6 (1.42 g, 5.37 mmol). After stirring overnight, water was added and the solution extracted with CH2Cl2 (3×). The combined organic extracts were concentrated to an oil. The oil was loaded onto a 10 g SCX ion exchange column equilibrated with MeOH. The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH. The fractions containing desired product were combined and concentrated to an oil. To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O. After stirring overnight the solution was concentrated to an oil to obtain the final compound. MS: 250.2 (M+1). the solution extracted with CH2Cl2 (3×) The combined organic extracts were concentrated to an oil The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH The fractions containing desired product concentrated to an oil To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O After stirring overnight the solution was concentrated to an oil