Isopropyl iodide → HCID 23003699, compound

HRID 396317Notes

Reaction equation

HRID 396317 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](C)([O-])[CH3:17].[K+].C(I)(C)C>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH:16]([CH3:17])[CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 192201-Benzyl-4-piperidoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 23003699HCID 23003699, compound

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 (6.0 g, 54.0 mmole) in tetrahydrofuran (50 ml) at 10° C. The reaction mixture was stirred for 15 min, isopropyl iodide (10 g, 54.0 mmole) was added at 10° C. The resulting mixture allowed coming at room temperature and stirred for 16 hr, 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-isopropylpiperid-4-one. Yield 3.3 g (28%), C15H21NO, m/z 232 (M+1).

Workup

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

Sources & evidence

ORD record
ord-938a72fc1eb94d4397f2500528123344
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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