Isobutyl iodide → 1-Benzyl-3-isobutylpiperidin-4-one

HRID 396323Notes

Reaction equation

HRID 396323 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:19])([O-])[CH3:17].[K+].C(I)C(C)C>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH2:15][CH:16]([CH3:19])[CH3:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 192201-Benzyl-4-piperidoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 230037241-Benzyl-3-isobutylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-benzylpiperidin-4-one (10 g, 53.0 mmole) was added to the stirred suspension of potassium tert. butoxide (7.0 g, 59.0 mmole) in tetrahydrofuran (50 ml) at 10° C. The reaction mixture was stirred for 15 min, isobutyl iodide (10.0 g, 54.0 mmole) was added at 10° C. The resulting mixture stirred for 16 hr at room temperature, refluxed for 3 hr and concentrated to dryness. The residue was triturated with water, extracted with ethyl acetate, dried (Na2SO4) and concentrated to give crude product, which was purified through column chromatography. Elute from 10% ethyl acetate in hexane afforded 1-benzyl-3-isobutylpiperidin-4-one. Yield 1.0 g (9%), C16H23NO, m/z 246 (M+1).

Workup

  1. stirringThe resulting mixture stirred for 16 hr at room temperature
  2. temperaturerefluxed for 3 hr
  3. concentrationconcentrated to dryness
  4. customThe residue was triturated with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified through column chromatography
  10. washElute from 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5ee3a94da0bd4786bb0bf1587c96211c
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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