Benzyl Chloride → 4-Benzyloxy-2,6-diethyl-2,3,6-trimethylpiperidine

HRID 616545Notes

Reaction equation

HRID 616545 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[H-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:17]([O:10][CH:7]1[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4][C:3]([CH2:1][CH3:2])([CH3:14])[CH:8]1[CH3:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-ol2×

Product 1

HCID 213303334-Benzyloxy-2,6-diethyl-2,3,6-trimethylpiperidineYield 48.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3.0 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidinol (Compound 1) in 30 ml of dry toluene was added, at 0° - 5° C, 0.65 g of sodium hydride (purity 52.9%). The mixture was refluxed by heating for 6 hours. After cooling the mixture, 1.9 g of benzyl chloride were added dropwise at 0° - 5° C and the resulting mixture was refluxed by heating for 4 hours. The reaction mixture was then washed with water and dried over anhydrous magnesium sulphate; the solvent was then distilled off. The residue was purified by column chromatography on silica gel using benzene as eluent, followed by distillation under reduced pressure. There were obtained 2.1 g of Compound 95 as a pale yellow oil (bp 120° - 124° C/0.2 mmHg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating for 6 hours
  3. additionwere added dropwise at 0° - 5° C
  4. temperaturethe resulting mixture was refluxed
  5. temperatureby heating for 4 hours
  6. washThe reaction mixture was then washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. distillationthe solvent was then distilled off
  9. customThe residue was purified by column chromatography on silica gel
  10. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-66e181b73924439fa39a5c13bf52f8ab
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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