Trifluoroiodomethane → HCID 23003695, compound

HRID 396299Notes

Reaction equation

HRID 396299 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.[H-].[Na+].[F:17][C:18](I)([F:20])[F:19].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:18]([F:20])([F:19])[F:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 16843TrifluoroiodomethaneHCID 192201-Benzyl-4-piperidoneHCID 24436Sodium SulfateHCID 24758Sodium hydride

Product 1

HCID 23003695HCID 23003695, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-benzylpiperidin-4-one (12 g, 63.5 mmole) was added to the stirred suspension of sodium hydride (3.0 g, 127.0 mmole) in tetrahydrofuran (100 ml) at −5° C. The reaction mixture was stirred for 15 min, trifluoromethyl iodide (25 g, 127.0 mmole) was bubbled over a period of 4 hr at −5° C. and stirring continued for 1 hr. The resulting mixture was stirred for 16 hr at ambient temperature, saturated sodium sulphate solution (20 ml) was added and diluted with ethyl acetate (200 ml). Ethyl acetate layer was separated, dried (Na2SO4) and concentrated to furnish crude product, which was purified through column chromatography. Elute from hexane afforded l-benzyl-3-trifluoromethylpiperidin-4-one as oil and 20% ethyl acetate in hexane gave the unreacted 1-benzylpiperidin-4-one (9.5 g). Yield 2.1 g (44%, based on reacted 1-benzyl piperidin-4-one), C13H14F3NO, m/z 258 (M+1), PMR (CDCl3): 2.54 (2H, m, H6), 3.02 (2H, m, H2), 3.6 (3H, m, H3 & H5), 4.36 (2H, s, N—CH2), 7.28 (5H, m, ArH).

Workup

  1. stirringstirring
  2. waitcontinued for 1 hr
  3. stirringThe resulting mixture was stirred for 16 hr at ambient temperature
  4. customEthyl acetate layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto furnish crude product, which
  8. customwas purified through column chromatography
  9. washElute from hexane

Sources & evidence

ORD record
ord-5325170a08194e10b6561c86d39ee990
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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