Sodium Hydroxide → 2-(4-n-Butylamino-2,2,6,6-tetramethylpiperidin-1-yl) ethanol

HRID 1955968Notes

Reaction equation

HRID 1955968 reaction equation
[CH2:1]([N:5]([CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH2:17][CH2:18][OH:19])[C:11]([CH3:21])([CH3:20])[CH2:10]1)C(=O)C)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>Cl>[CH2:1]([NH:5][CH:9]1[CH2:10][C:11]([CH3:20])([CH3:21])[N:12]([CH2:17][CH2:18][OH:19])[C:13]([CH3:15])([CH3:16])[CH2:14]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19073314N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide

Product 1

HCID 543503372-(4-n-Butylamino-2,2,6,6-tetramethylpiperidin-1-yl) ethanolYield 74.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 12.6 g (42.2 mmol) of N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide [Example 1bη2] in 180 ml of 2N hydrochloric acid is refluxed for 48 hours. The reaction mixture is then cooled 0°-5° C. and, after addition of 40 ml of 30% sodium hydroxide solution, extracted twice with toluene. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel with the solvent system ethyl acetate/ethanol/triethylamine=50:2:1 gives 8.1 g (68%) of 2-(4-n-butylamino-2,2,6,6-tetramethylpiperidin-1-yl) ethanol (208) in the form of a white powder, m.p. 106°-111° C.

Workup

  1. temperatureThe reaction mixture is then cooled 0°-5° C.
  2. extractionextracted twice with toluene
  3. washThe organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-70052ea9a9a147ff902a7cf1e12a74ea
Source dataset
uspto-grants-1998_07
Patent number
US05777113

Reaction notes

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