1-chloro-2,2,6,6-tetramethylpiperidine

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of 2,2,6,6-tetramethylpiperidine are mixed with water and 6.42 g, 0.6 eq., of calcium hydroxide, and the suspension is cooled to 5° C. Over a period of 1.5 hours, 10.8 g, 1.1 eq. of chlorine gas are introduced, then nitrogen gas is used to drive out the excess chlorine and the mixture is warmed to RT. After separating the phases, washing the aqueous phase with 25 ml of dichloromethane, drying the combined organic phases with magnesium sulphate and distilling off the dichloromethane in vacuo, 24.2 g, 99%, of 1-chloro-2,2,6,6-tetramethylpiperidine are obtained. the mixture is warmed to RT After separating the phases washing the aqueous phase with 25 ml of dichloromethane drying the combined organic phases with magnesium sulphate distilling off the dichloromethane in vacuo, 24.2 g, 99%

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of 2,2,6,6-tetramethylpiperidine are mixed with 40.7 g, 1.1 eq, of 15% sodium hydroxide solution and cooled to 5 to 10° C. Over a period of 1.5 hours, 10.8 g, 1.1 eq. of chlorine gas are introduced, then nitrogen gas is used to drive out the excess chlorine and the mixture is warmed to room temperature (RT). After separating the phases, washing the aqueous phase with 25 ml of dichloromethane, drying the combined organic phases with magnesium sulphate and distilling off the dichloromethane in vacuo, 24.2 g, 99%, of 1-chloro-2,2,6,6-tetramethylpiperidine are obtained. the mixture is warmed to room temperature (RT) After separating the phases washing the aqueous phase with 25 ml of dichloromethane drying the combined organic phases with magnesium sulphate distilling off the dichloromethane in vacuo, 24.2 g, 99%