Formaldehyde → 4-Benzyloxy-2,6-diethyl-1,2,3,6-tetramethylpiperidine

HRID 616548Notes

Reaction equation

HRID 616548 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH2:16][CH3:17])([CH3:15])[NH:12][C:11]([CH2:19][CH3:20])([CH3:18])[CH:10]1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:24](=O)(O)[O-].[Na+]>C(O)=O>[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH2:16][CH3:17])([CH3:15])[N:12]([CH3:24])[C:11]([CH2:19][CH3:20])([CH3:18])[CH:10]1[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 213303334-Benzyloxy-2,6-diethyl-2,3,6-trimethylpiperidine

Product 1

HCID 213304124-Benzyloxy-2,6-diethyl-1,2,3,6-tetramethylpiperidine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 1.0 g of 4-benzyloxy-2,6-diethyl-2,3,6-trimethylpiperidine (Compound 95 - prepared as described in Preparation 5) were added 0.52 g of formic acid and 1.22 g of 37 % formalin at 0° - 5° C. The mixture was stirred at room temperature and then refluxed by heating for 3 hours. When the reaction was complete, the reaction mixture was adjusted to a pH value of 8.0 by addition of a 5 % aqueous solution of sodium bicarbonate; the mixture was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulphate and the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel using benzene as eluent; the resulting product was then distilled under reduced pressure, giving 0.6 g of Compound 100 as a pale yellow liquid (bp 132° - 135° C/0.2 mmHg).

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 3 hours
  3. extractionthe mixture was then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulphate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. distillationthe resulting product was then distilled under reduced pressure

Sources & evidence

ORD record
ord-4b512f6dc0ba47f8bb1246af68a603d3
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

Loading…