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

HRID 1479701Notes

Reaction equation

HRID 1479701 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-].[Ca+2].[OH-].[Cl:14]Cl>O>[Cl:14][N:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:10])[CH3:1]

Participants

5

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 24526Chlorine2×HCID 6093208Calcium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

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.

Workup

  1. temperaturethe mixture is warmed to 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-6ba3ec8960bf4605bc06da9ac379ce66
Source dataset
uspto-grants-2016_08
Patent number
US09409863B2

Reaction notes

Loading…