Benzyl Chloride → HCID 22160716, compound

HRID 847668Notes

Reaction equation

HRID 847668 reaction equation
[C:1]([O:18][CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[N:22]([CH3:27])[C:21]([CH3:29])([CH3:28])[CH2:20]1)(=[O:17])[CH2:2][C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)=[O:4].[H-].[Na+].[H][H].[CH2:34](Cl)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[CH2:34]([C:2]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:1]([O:18][CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[N:22]([CH3:27])[C:21]([CH3:29])([CH3:28])[CH2:20]1)=[O:17])[C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)=[O:4])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 7503Benzyl Chloride2×HCID 24758Sodium hydride3×HCID 20343478Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) propanedioateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22160716HCID 22160716, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

205 g of bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) malonate, prepared according to known methods, are heated with 12 g of sodium hydride in 500 ml of absolute toluene for 6 hours under reflux. After this time the evolution of hydrogen has ceased and virtually no particles of sodium hydride can be detected in the reaction mixture. The mixture is cooled to 50°, 63 g of benzyl chloride are added dropwise in about 30 minutes and the mixture is then stirred for 1 hour under reflux. It is then again cooled to about 50°, a further 12 g of sodium hydride are added and the mixture is heated under reflux until the evolution of hydrogen has completely ceased (about 6 hours). It is then again cooled to 50°, 63 g of benzyl chloride are added dropwise in about 30 minutes and the mixture is then stirred for 3 hours under reflux. The reaction solution is washed with three times 200 ml of water, dried over sodium sulphate and evaporated. Crystallisation of the residue from hexane gives bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) dibenzylmalonate (compound 7) which has a melting point of 121°-122°.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture is cooled to 50°
  3. temperatureunder reflux
  4. temperatureIt is then again cooled to about 50°
  5. temperaturethe mixture is heated
  6. custom(about 6 hours)
  7. temperatureIt is then again cooled to 50°
  8. stirringthe mixture is then stirred for 3 hours
  9. temperatureunder reflux
  10. washThe reaction solution is washed with three times 200 ml of water
  11. dry with materialdried over sodium sulphate
  12. customevaporated
  13. customCrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-4774f95afe054c3b8935b530ce3a9c03
Source dataset
uspto-grants-1981_10
Patent number
US04293468

Reaction notes

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