2,2,6,6-Tetramethyl-4-piperidone → 4-Hydroxy-2,2,6,6-tetramethylpiperidine

HRID 569191Notes

Reaction equation

HRID 569191 reaction equation
OCC[N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]1([CH3:14])[CH3:13].CC1(C)NC(C)(C)CC(=O)C1>O>[CH3:13][C:5]1([CH3:14])[CH2:6][CH:7]([OH:12])[CH2:8][C:9]([CH3:11])([CH3:10])[NH:4]1

Participants

4

Reactant 2

HCID 132202,2,6,6-Tetramethyl-4-piperidone2×HCID 1043011-(2-Hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol

Product 1

HCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Accordingly, the invention relates to a process for the preparation of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol from triacetoneamine, which comprises reducing triacetoneamine in a manner known per se by catalytic hydrogenation in water or in a polar organic solvent or in a mixture thereof with water, to give 2,2,6,6-tetramethyl-4-piperidinol, adding a catalytic amount of an inorganic or organic acid to the solution of 2,2,6,6-tetramethyl-4-piperidinol as obtained or after concentrating the solution by distillation, without further purification and/or isolation of the intermediate, with the proviso that, if the solution of the intermediate is concentrated, the addition of acid is made before or after the distillation, and that the concentrated solution or melt may be diluted again with the same solvent or with another solvent, and subsequently reacting said solution or melt of 2,2,6,6-tetramethyl-4-piperidinol with ethylene oxide in a molar excess of 1-35% in the temperature range from 60°-170° C.

Sources & evidence

ORD record
ord-6f01c958f5bc47a7a62711c28e1bd3bd
Source dataset
uspto-grants-1988_03
Patent number
US04731448

Reaction notes

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