Dichloromethane → HCID 59363373, compound

HRID 905964Notes

Reaction equation

HRID 905964 reaction equation
[C:1]([O:5]C(=O)NC1CCCN(CC(F)(F)F)C1)(C)(C)C.CC[N:22]([CH:26]([CH3:28])C)[CH:23]([CH3:25])C.[C:29](Cl)(=[O:31])[CH3:30].[CH2:33](Cl)Cl>>[C:29]([N:22]1[CH2:23][CH2:25][C:1](=[O:5])[CH:28]([CH3:33])[CH2:26]1)(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67386443Racemic [1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 59363373HCID 59363373, compoundYield 94%

Conditions

Temperature
25 °C

Procedure

To a suspension of the product of step 1 in DCM at 0° C., DIPEA (4 eqv) was added slowly and stirred for 30 minutes at 25° C. The reaction mixture was cooled again to 0° C. and acetyl chloride (1.1 eqv) was added slowly. The resulting mixture was stirred at 25° C. for 16 hrs before being quenched by addition of saturated aqueous NaHCO3. The aqueous layer was back extracted three times with DCM. The combined organics were washed with H2O, dried (Na2SO4), filtered and evaporated. The residue was purified by SiO2 flash chromatography to give racemic 1-acetyl-3-methyl-piperidin-4-one (94% over two steps).

Workup

  1. temperatureThe reaction mixture was cooled again to 0° C.
  2. stirringThe resulting mixture was stirred at 25° C. for 16 hrs
  3. custombefore being quenched by addition of saturated aqueous NaHCO3
  4. extractionThe aqueous layer was back extracted three times with DCM
  5. washThe combined organics were washed with H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-fcecddb673734e6fbecb6ae7b1435cca
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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