N-(3-bromopropyl)acetamide

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

Procedure: 191 mg of 3-(1-piperidinylmethyl)phenol was dissolved in 10 ml of ethanol, and 116 mg of potassium hydroxide was added. The mixture was heated under reflux, and a solution of 360 mg of 3-acetamino-1-bromopropane in 3 ml of ethanol. The reaction mixture was heated under reflux for 8 hours, and the solvent was distilled off under reduced pressure. Water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 205 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide as an oil. The resulting product coincided with the product obtained in Example 2. The mixture was heated under reflux The reaction mixture was heated under reflux for 8 hours the solvent was distilled off under reduced pressure Water was added the mixture was extracted with chloroform The organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by TLC (developing solvent: chloroform/methanol=9/l)

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of thiophene-2-thiol (1.8 g, 15.9 mmol, 1.0 eq), N-(3-bromopropyl) acetamide (4.3 g, 23.9 mmol, 1.5 eq) and K2CO3 (4.4 g, 31.8 mmol, 2.0 eq) in CH2Cl2 (50 mL) was stirred at 23° C. for 1 hour. Then the mixture was extracted with CH2Cl2. (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated to give white solid N-(3-(thiophen-2-ylthio)propyl)acetamide (2.5 g, 72.8%); LC-MS (m/z)=215.9 [M+H]+. Then the mixture was extracted with CH2Cl2 The combined organic layers were dried (Na2SO4) filtered concentrated

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

Procedure: 191 mg of 3-(1-piperidinylmethyl)phenol was dissolved in 10 ml of ethanol, and 116 mg of potassium hydroxide was added. The mixture was heated under reflux, and a solution of 360 mg of 3-acetamino-1-bromopropane in 3 ml of ethanol. The reaction mixture was heated under reflux for 8 hours, and the solvent was distilled off under reduced pressure. Water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 205 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide as an oil. The resulting product coincided with the product obtained in Example 2. The mixture was heated under reflux The reaction mixture was heated under reflux for 8 hours the solvent was distilled off under reduced pressure Water was added the mixture was extracted with chloroform The organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by TLC (developing solvent: chloroform/methanol=9/l)