Sodium Hydroxide → Tetradecyl 2,2,6,6-tetramethyl-4-piperidinyl carbonate

HRID 1439958Notes

Reaction equation

HRID 1439958 reaction equation
[C:1](Cl)(=[O:17])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[CH3:20][C:21]1([CH3:30])[CH2:26][CH:25]([OH:27])[CH2:24][C:23]([CH3:29])([CH3:28])[NH:22]1.[OH-].[Na+]>ClCCl.O>[C:1](=[O:17])([O:27][CH:25]1[CH2:26][C:21]([CH3:30])([CH3:20])[NH:22][C:23]([CH3:29])([CH3:28])[CH2:24]1)[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 92493Tetradecyl chloroformateHCID 189851222,2,6,6-Tetramethylpiperidinol-4 hydrochloride

Product 1

HCID 15217567Tetradecyl 2,2,6,6-tetramethyl-4-piperidinyl carbonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

27.7 g (0.1 mol) of tetradecyl chlorocarbonate are added slowly to a solution of 19.4 g (0.1 mol) of 2,2,6,6-tetramethyl-4-piperidinol hydrochloride in 150 ml of dichloromethane, maintaining the temperature at between 0° C. and 5° C. After the end of the addition, the mixture is stirred for 2 hours at ambient temperature, and a solution of 8.8 g (0.22 mol) of NaOH in 50 ml of water is then added slowly, with cooling to -10° C.

Workup

  1. temperaturemaintaining the temperature at between 0° C. and 5° C
  2. additionAfter the end of the addition
  3. temperaturewith cooling to -10° C.

Sources & evidence

ORD record
ord-e092de717f9c473091ad8c8cfb0647bd
Source dataset
uspto-grants-1996_03
Patent number
US05496875

Reaction notes

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