2-iodohexane

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

Procedure: 4-Hydroxypiperidine (2.02 g, 20 mmol) was dissolved in 100 mL of methyl ethylketone. To this stirred mixture was added 2-iodohexane (1.5 mL, 10 mmol) and the resulting solution was heated at reflux for 1.5 hours. The mixture was allowed to cool and was then washed with saturated aqueous sodium bicarbonate (3×75 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated, and the residue was dried overnight under house vacuum to yield 1.184 g (64%) of the title compound which was used without further purification. 1H NMR consistent with desired product. MS(FD) 186(M+). the resulting solution was heated at reflux for 1.5 hours to cool was then washed with saturated aqueous sodium bicarbonate (3×75 mL) The organic layer was dried over magnesium sulfate filtered evaporated the residue was dried overnight under house vacuum

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

Procedure: 4-Hydroxypiperidine (2.02 g, 20 mmol) was dissolved in 100 mL of methyl ethylketone. To this stirred mixture was added 2-iodohexane (1.5 mL, 10 mmol) and the resulting solution was heated at reflux for 1.5 hours. The mixture was allowed to cool and was then washed with saturated aqueous sodium bicarbonate (3×75 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated, and the residue was dried overnight under house vacuum to yield 1.184 g (64%) of the title compound which was used without further purification. 1H NMR consistent with desired product. MS(FD) 186(M+). the resulting solution was heated at reflux for 1.5 hours to cool was then washed with saturated aqueous sodium bicarbonate (3×75 mL) The organic layer was dried over magnesium sulfate filtered evaporated the residue was dried overnight under house vacuum

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

Procedure: The same procedure as in Example 6 was repeated except that the molar ratio of 2-iodohexane to o-aminophenol was changed to 0.8, the 2-iodohexane was dropped over 4.5 h, and then the reaction mixture was stirred at room temperature for 0.5 h. As a result, it was confirmed that the rate of conversion of o-aminophenol was 71%, the selectivity to the N-monoalkylated compound was 86%, and the oxygen absorption initiation time as an index of determining an oxidation-inhibiting property thereof was 320 min. the oxygen absorption initiation time as an index thereof was 320 min.

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

Procedure: The same procedure as in Example 4 was repeated except for using 2-iodohexane in place of 2-iodobutane, to conduct the reaction. As a result, it was confirmed that the rate of conversion of o-aminophenol was 93%, the selectivity to the N-monoalkylated compound was 41% and the oxygen absorption initiation time as an index of determining an oxidation-inhibiting property thereof was 320 min. the reaction the oxygen absorption initiation time as an index

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

Procedure: 4-Hydroxypiperidine (2.02 g, 20 mmol) was dissolved in 100 mL of methyl ethylketone. To this stirred mixture was added 2-iodohexane (1.5 mL, 10 mmol) and the resulting solution was heated at reflux for 1.5 hours. The mixture was allowed to cool and was then washed with saturated aqueous sodium bicarbonate (3×75 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated, and the residue was dried overnight under house vacuum to yield 1.184 g (64%) of the title compound which was used without further purification. 1H NMR consistent with desired product. MS(FD) 186(M+). the resulting solution was heated at reflux for 1.5 hours to cool was then washed with saturated aqueous sodium bicarbonate (3×75 mL) The organic layer was dried over magnesium sulfate filtered evaporated the residue was dried overnight under house vacuum