Hydrochloric Acid → HCID 23003721, compound

HRID 396331Notes

Reaction equation

HRID 396331 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([Si](C)(C)C)([F:19])[F:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([C:17]([F:19])([F:18])[F:16])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 23003721HCID 23003721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dry tetrahydrofuran (20 ml) was added to a stirred mixture of 1-benzyl-3-methylpiperidin-4-one (4 g, 19.7 mmole) and (Trifluoromethyl) trimethylsilane (3.35 g, 23.64 mmole) at 0° C. and stirred for 5 min. Tetrabutyl ammonium fluoride (0.05 g) was added to it at 0° C. and stirred for another 30 min at 0° C. The reaction mixture was allowed to warm to room temperature, stirred for 3 hr, acidified with 2N HCl to pH 2 and extracted with ether (3×50 ml). Ether extract was dried (Na2SO4) and concentrated in vacuum to give 1-benzyl-3-methyl-4-hydroxy-4-trifluoromethylpiperidine. Yield 5.1 g (95%), C14H18F3NO, m/z 274 (M+1).

Workup

  1. stirringstirred for another 30 min at 0° C
  2. stirringstirred for 3 hr
  3. extractionextracted with ether (3×50 ml)
  4. extractionEther extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a7951bb9c67f4f748b64bfc796fa0879
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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