Tetrabutylammonium Fluoride → HCID 22645417, compound

HRID 2414273Notes

Reaction equation

HRID 2414273 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:25])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][Si](C)(C)C)[CH:14]=2)[CH:9]([CH3:26])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.ClCCl.O>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:25])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[CH:20])[CH:14]=2)[CH:9]([CH3:26])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22645392HCID 22645392, compound

Product 1

HCID 22645417HCID 22645417, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-hexyl-3,4-dimethyl-4-{3-[2-(trimethylsilyl)ethynyl]-phenyl}piperidine (Preparation 4, 150 mg, 0.40 mmol) in tetrahydrofuran (2 mL) was cooled to -70° C. and tetrabutylammonium fluoride (1.0 M in THF, 0.41 mL, 0.41 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature gradually before being diluted with dichloromethane (10 mL) and water (10 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2×10 mL). The combined organics were dried (Na2SO4) and the solvent evaporated in vacuo. The oily yellow residue was purified by column chromatography on silica gel (10 g) eluted with ethyl acetate:hexane 0.880 ammonia (10:89:1) to give the title compound as an oil (100 mg).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was further extracted with dichloromethane (2×10 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customthe solvent evaporated in vacuo
  5. customThe oily yellow residue was purified by column chromatography on silica gel (10 g)
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-b974306783e147b3ab8f9740b0582e9c
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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