Potassium Hydroxide → HCID 57743035, compound

HRID 1896400Notes

Reaction equation

HRID 1896400 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][N:6]([CH3:10])[C:7]=1[CH2:8][NH2:9].[O-]S([O-])(=O)=O.[Na+].[Na+].[OH-].[K+].Br[CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].[H-].[Na+]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[N:4]=[CH:5][N:6]([CH3:10])[C:7]=1[CH2:8][N:9]1[CH2:21][CH2:22][CH2:23][C:24]1=[O:25]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 24758Sodium hydride2×HCID 702254-Bromobutyryl chlorideHCID 53629168HCID 53629168, compound

Product 1

HCID 57743035HCID 57743035, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

In a 50 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, 1-(4-methoxy-1-methyl-1H-imidazol-5-yl)methanamine x94 (0.37 g, 2.62 mmol), Na2SO4 (0.37 g, 2.62 mmol) and powdered molecular sieves are stirred in CH2Cl2 (25 ml) at 0° C. At this temperature, powdered KOH (0.53 g, 9.44 mmol) and a solution of tetra-n-butyl ammonium bromide (48 mg, 0.13 mmol) in CH2Cl2 (5 ml) are added. The mixture is stirred for 0.25 h at 0° C. and 4-bromobutanoyl chloride (366 μl, 3.14 mmol) is added dropwise. Stirring is continued for 2 h. The mixture is filtered on Celite and evaporated in vacuo. The residue is dissolved in DMF (25 ml) and NaH (60% dispersion in oil, 0.12 g, 3.14 mmol) is added. The mixture is stirred at room temperature for 16 h. An additional portion of NaH (0.52 mmol) is added and the mixture is stirred for 4 more hours at room temperature. The mixture is then diluted with 30 ml of CH2Cl2, filtered on Celite and concentrated to dryness. The residue is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v)) and recrystallized from diisopropyl ether to afford 150 mg of 1-[(4-methoxy-1-methyl-1H-imidazol-5-yl)methyl]pyrrolidin-2-one 120.

Workup

  1. stirringStirring
  2. waitis continued for 2 h
  3. filtrationThe mixture is filtered on Celite
  4. customevaporated in vacuo
  5. dissolutionThe residue is dissolved in DMF (25 ml)
  6. stirringThe mixture is stirred at room temperature for 16 h
  7. stirringthe mixture is stirred for 4 more hours at room temperature
  8. filtrationfiltered on Celite
  9. concentrationconcentrated to dryness
  10. customThe residue is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v))
  11. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8adf97072a454d26ab2563e9b90ccbec
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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