Isobutyryl chloride → HCID 18538606, compound

HRID 412914Notes

Reaction equation

HRID 412914 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:20]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])[CH2:10][CH2:9]2)=[CH:7][CH:6]=1)(=[O:24])[CH:21]([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 8977951‐(4‐Benzylpiperidin‐1‐yl)‐2,2,2‐trifluoroethan‐1‐oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18538606HCID 18538606, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-benzyl-1-(trifluoroacetyl)piperidine (4.34 g, 16.0 mmol) and isobutyryl chloride (2.18 mL, 20.8 mmol) in dichloromethane (50 mL) was added aluminum chloride (5.33 g, 40.0 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water (50 g), the organic layer was separated and the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with saturated aqueous sodium bicarbonate solution (3×15 mL), brine (15 mL), dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using ethyl acetate/hexane (1/19 to 1/9) as eluent to afford the title compound (3.60 g, 10.5 mmol, 66%) as a colorless oil.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers
  3. washwere washed with saturated aqueous sodium bicarbonate solution (3×15 mL), brine (15 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c5a73df50a604f5bb5c36537d62d3768
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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