Hydrochloric Acid → 4-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-

HRID 1276643Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([OH:10])[C:4]([CH3:12])([CH3:11])[CH2:3]1.OO.Cl.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17]>O>[OH:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[N:5]([O:10][CH2:17][C:16]([OH:20])([CH3:19])[CH3:18])[C:4]([CH3:12])([CH3:11])[CH2:3]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 17.2 g (100 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine dissolved in 50 mL of water and a solution of 25.3 g (0.37 mol) of 50% aqueous hydrogen peroxide are added simultaneously over 3-3.5 hours at 40° C. to a mixture of 0.27 g (1.0 mmol) of ferric chloride hexahydrate, 25 mL of water, 1.1 mL of 37% hydrochloric acid and 200 mL of tert-butyl alcohol. About two hours into the addition, 0.5 mL of 37% hydrochloric acid is added to the reaction mixture. After the peroxide addition is complete, 1.2 mL of 37% hydrochloric acid is added and the reaction mixture is heated at 40-50° C. for 3.5 hours. The reaction mixture is stirred overnight at room temperature. The reaction is completed by adding two portions of 0.3 mL of 37% hydrochloric acid while heating the reaction mixture at 45° C. for 5.5 hours. Work-up is done as in Example 20 and affords 21.5 g (88% yield) of the title compound as a white solid. Gas chromatography shows the product has a purity greater than 96%.

Workup

additionis added to the reaction mixture
temperaturewhile heating the reaction mixture at 45° C. for 5.5 hours

Sources & evidence

ORD record: ord-d69aabb74f4d4348bf53ac1c4fbdcdfb
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166212

Reaction notes

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