Potassium Carbonate → N-(1-(4-formylphenyl)pyrrolidin-3-yl)-N-methylacetamide

HRID 591664Notes

Reaction equation

HRID 591664 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][N:11]([CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)[C:12](=[O:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:17]2[CH2:18][CH2:19][CH:15]([N:11]([CH3:10])[C:12](=[O:14])[CH3:13])[CH2:16]2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 130411303-(N-Acetyl-N-methylamino)pyrrolidine

Product 1

HCID 86662025N-(1-(4-formylphenyl)pyrrolidin-3-yl)-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 4-fluorobenzaldehyde (2.01 g, 16.2 mmol) and N-methyl-N-(pyrrolidin-3-yl)acetamide (1.92 g, 13.5 mmol) in DMF (20 mL) was treated with K2CO3 (2.24 g, 16.2 mmol). The mixture was heated at 120° C. under nitrogen for 18 hours, cooled to room temperature, diluted with ethyl acetate (150 mL), washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 100% ethyl acetate to 10% methanol/ethyl acetate, to afford N-(1-(4-formylphenyl)pyrrolidin-3-yl)-N-methylacetamide.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 100% ethyl acetate to 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-ddcef53de89a476cb05e770383f33589
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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