2,2,6,6-Tetramethylpiperidine → Piperidine, 1-chloro-2,2,6,6-tetramethyl-

HRID 1479700Notes

Reaction equation

HRID 1479700 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.[OH-].[Na+].[Cl:13]Cl>>[Cl:13][N:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:10])[CH3:1]

Participants

4

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 14798Sodium HydroxideHCID 24526Chlorine2×

Product 1

HCID 141712Piperidine, 1-chloro-2,2,6,6-tetramethyl-

Conditions

Temperature
7.5 °C

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.

Workup

  1. temperaturethe mixture is warmed to room temperature (RT)
  2. customAfter separating the phases
  3. washwashing the aqueous phase with 25 ml of dichloromethane
  4. dry with materialdrying the combined organic phases with magnesium sulphate
  5. distillationdistilling off the dichloromethane in vacuo, 24.2 g, 99%

Sources & evidence

ORD record
ord-38bd88183b6749e990adb0de892e03ae
Source dataset
uspto-grants-2016_08
Patent number
US09409863B2

Reaction notes

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