Formaldehyde → 4-Piperidinol, 1,2,2,6,6-pentamethyl-

HRID 1414154Notes

Reaction equation

HRID 1414154 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[CH2:12]=O.[OH-].[Na+]>C(O)=O>[CH3:12][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 18 grams of commercially available 2,2,6,6-tetramethyl-4-hydroxypiperidine, 18 grams of an aqueous solution containing 37% of formaldehyde and 4 milliliters of formic acid containing 1% water is placed in a 100-ml., round-bottomed flask and heated on a steam bath for 7 hours. The contents are cooled, made basic with sodium hydroxide and extracted with ether. The ether extract is dried using anhydrous magnesium sulfate and the ether evaporated. The residue, a white solid, is purified by sublimation at 90°C. at 0.05 torr. The purified 1,2,2,6,6-pentamethyl-4-hydroxypiperidine has a melting point of 70°-71°C.

Workup

  1. temperature, round-bottomed flask and heated on a steam bath for 7 hours
  2. temperatureThe contents are cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. customis dried
  6. customthe ether evaporated
  7. customThe residue, a white solid, is purified by sublimation at 90°C. at 0.05 torr

Sources & evidence

ORD record
ord-569835ea506e49a49a0d4ed9bcb576de
Source dataset
uspto-grants-1977_01
Patent number
US04001189

Reaction notes

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