Sodium Hydroxide → HCID 23136891, compound

HRID 238287Notes

Reaction equation

HRID 238287 reaction equation
C(N1CCC(C)(O)CC1)C1C=CC=CC=1.[Cl-:16].[Cl-].[Cl-].[Al+3].[OH-].[Na+].[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:36]2[CH:41]=[CH:40][C:39](Cl)=[CH:38][CH:37]=2)([CH3:35])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClC1C=CC=CC=1>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[Cl:16])([CH3:35])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-olHCID 18675725HCID 18675725, compound

Product 1

HCID 23136891HCID 23136891, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

1-Benzyl-4-methyl-piperidin-4-ol (4.5 g) was dissolved in chlorobenzene (50 mL). Aluminium trichloride (15 g) was added portion wise and the mixture then heated at reflux for 0.5 hours. The mixture was then allowed to cool and poured over ice. The resulting solution was treated with sodium hydroxide until basic and the products extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by silica chromatography eluting with a mixture of ethyl acetate and hexane. The fractions containing the desired products were combined and the solvent removed by evaporation to give a 4:1 mixture of the title compound and 1-benzyl-4-(4-chloro-phenyl)-4-methyl-piperidine which was used directly without further purification.

Workup

  1. temperaturethe mixture then heated
  2. temperatureat reflux for 0.5 hours
  3. temperatureto cool
  4. additionpoured over ice
  5. extractionextracted into ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed by evaporation under vacuum
  9. customThe residue was purified by silica chromatography
  10. washeluting with a mixture of ethyl acetate and hexane
  11. additionThe fractions containing the desired products
  12. customthe solvent removed by evaporation
  13. customto give

Sources & evidence

ORD record
ord-9c40489495e845968a14d9d92c9f0591
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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