1,4-Dioxane hydrochloride → 4-(4-Chlorophenyl)-3,3-dimethylpiperidin-4-ol

HRID 242563Notes

Reaction equation

HRID 242563 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([OH:14])[C:10]([CH3:23])([CH3:22])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][C:10]2([CH3:22])[CH3:23])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 593412124-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 231311434-(4-Chlorophenyl)-3,3-dimethylpiperidin-4-ol

Procedure

4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.73 mmol) was dissolved in 4M HCl/Dioxane (2 mL, 8 mmol). The solution was stirred at room temperature for about 4 hours. The solvent was removed in vacuo. The residue was quenched with aqueous sodium hydroxide, extracted with ethyl acetate, and the organic layers were dried over sodium sulfate and evaporated in vacuo to yield the title compound as a yellow solid. The mixture was carried on to the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was quenched with aqueous sodium hydroxide
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layers were dried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-92aae535003c45c2a748a8c53874f5ce
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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