HCID 20295617, compound → HCID 70569303, compound

HRID 1389867Notes

Reaction equation

HRID 1389867 reaction equation
[ClH:1].[F:2][C:3]([F:23])([F:22])[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([CH:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[OH:15])[CH:5]=1>C(O)(=O)C.S(=O)(=O)(O)O.O.[O-2].[O-2].[O-2].[Cr+6]>[ClH:1].[NH:19]1[CH2:20][CH2:21][CH:16]([C:14]([C:6]2[CH:5]=[C:4]([C:3]([F:2])([F:22])[F:23])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)=[O:15])[CH2:17][CH2:18]1

Participants

6

Reactant 1

HCID 20295617HCID 20295617, compound

Product 1

HCID 70569303HCID 70569303, compound

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A chilled, stirred solution of 124 g (0.4 mole) of α-(4-trifluoromethyl-2-naphthyl)-4-piperidinemethanol hydrochloride in 600 ml of acetic acid, 40 ml of 25% sulfuric acid and 72 ml of water is added with stirring to 26.5 g (0.27 mole) of chromium trioxide in 30 ml of acetic acid over a period of 11/2 hours, during which time an additional 20 ml of water is added. The mixture is stirred for 1/2 hour at a temperature of less than 9° C. The solvent is removed under vacuum and the residue treated with excess sodium hydroxide and extracted with ether and with chloroform. The combined extracts are washed with water, dried over MgSO4 and filtered. To the filtrate is added additional chloroform and ethereal HCl. The resulting precipitate is filtered off and recrystallized from isopropyl alcohol to yield 4-trifluoromethyl-2-naphthyl 4-piperidyl ketone hydrochloride.

Workup

  1. additionis added
  2. additionis added
  3. customThe solvent is removed under vacuum
  4. additionthe residue treated with excess sodium hydroxide
  5. extractionextracted with ether and with chloroform
  6. washThe combined extracts are washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. additionTo the filtrate is added additional chloroform and ethereal HCl
  10. filtrationThe resulting precipitate is filtered off
  11. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-4712d7e89e6246b79af3879f5df5b529
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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