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

HRID 917093Notes

Reaction equation

HRID 917093 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-a5e0bc4e1be848b7be8758a67b446d2f
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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