Ethanol → HCID 15428772, compound

HRID 1857947Notes

Reaction equation

HRID 1857947 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([CH2:26][N+:27]#[C-])(C1C=CC(C)=CC=1)(=O)=O.C(O)C.CC(C)([O-])C.[K+]>COCCOC>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:26]#[N:27])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 90583N-Benzoyl-4-piperidoneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 15428772HCID 15428772, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1-benzoyl-4-piperidone (2.0 g, 9.8 mmol), tosylmethyl isocyanide (2.5 g, 12.8 mmol) and ethanol (1.0 mL, 17.1 mmol) in 30 mL DME was cooled in an ethanol/ice bath, and potassium tert-butoxide was added at such a rate to maintain the reaction temperature at <10° C. The cold bath was removed, and the reaction was allowed to stir overnight at room temperature. The solids were removed by filtration, rinsed with DME, and the filtrate was evaporated. The residue was dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered through silica gel, and concentrated to give 2.14 g (66%) of a slightly yellow oil.

Workup

  1. temperaturewas cooled in an ethanol/ice bath
  2. temperatureto maintain the reaction temperature at <10° C
  3. customThe cold bath was removed
  4. customThe solids were removed by filtration
  5. washrinsed with DME
  6. customthe filtrate was evaporated
  7. dissolutionThe residue was dissolved in EtOAc
  8. washwashed with water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered through silica gel
  11. concentrationconcentrated
  12. customto give 2.14 g (66%) of a slightly yellow oil

Sources & evidence

ORD record
ord-ad5b445e4a3e4e02b7d1cf9be4935cde
Source dataset
uspto-grants-2000_11
Patent number
US06150362

Reaction notes

Loading…