N,N'-Dimethylethylenediamine → 3,3-Dimethyl-1-(1-methyl-1h-pyrazol-3-yl)-2-pyrrolidinone

HRID 632775Notes

Reaction equation

HRID 632775 reaction equation
I[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[CH3:8][C:9]1([CH3:15])[CH2:13][CH2:12][NH:11][C:10]1=[O:14].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>COC1CCCC1.[Cu]I>[CH3:8][C:9]1([CH3:15])[CH2:13][CH2:12][N:11]([C:2]2[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=2)[C:10]1=[O:14]

Participants

8

Reactant 5

HCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 51149083,3-Dimethylpyrrolidin-2-oneHCID 133340573-Iodo-1-methyl-1H-pyrazole

Product 1

HCID 1180612443,3-Dimethyl-1-(1-methyl-1h-pyrazol-3-yl)-2-pyrrolidinoneYield 91.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 138539Cyclopentyl methyl etherSolvent

Procedure

A solution of 3-iodo-1-methyl-1H-pyrazole (200 mg), 3,3-dimethylpyrrolidin-2-one (109 mg), copper(I) iodide (73 mg), N1,N2-dimethylethane-1,2-diamine (0.083 mL) and tripotassium phosphate (408 mg) in cyclopentyl methyl ether (4 mL) was stirred overnight at 120° C. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (170 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02fce6b6165b4d359ca6ea2341406d0f
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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