Benzyl Bromide → 4-Piperidinol, 2,2,6,6-tetramethyl-1-(phenylmethyl)-

HRID 597548

Reaction equation

HRID 597548 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](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:12]([N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 1036024-Piperidinol, 2,2,6,6-tetramethyl-1-(phenylmethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 31.4 parts of 2,2,6,6-tetramethylpiperidin-4-ol and 17.1 parts of benzyl bromide in 125 parts of ethyl alcohol was heated under reflux conditions for 96 hours. The cooled reaction mixture was filtered to remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide formed during the reaction and the ethyl alcohol solvent was removed by distillation under reduced pressure. Purification of the residue by chromatography on a aluminia column using chloroform as the solvent gave 1-benzyl-2,2,6,6-tetramethylpiperidin-4-ol having a melting point of 151°-2°C and the following elemental analysis by weight

Workup

  1. temperaturewas heated under reflux conditions for 96 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide
  5. customformed during the reaction
  6. customthe ethyl alcohol solvent was removed by distillation under reduced pressure
  7. customPurification of the residue by chromatography on a aluminia column

Sources & evidence

ORD record
ord-fabf840c398a4b41a2b3105305022d47
Source dataset
uspto-grants-1977_03
Patent number
US04014887

Linked notes

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