Dimethylamine → HCID 19600081, compound

HRID 611230Notes

Reaction equation

HRID 611230 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([N:5]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][O:13][C:7]=2[CH2:6]1)=[O:4].[CH3:16][NH:17][CH3:18].[CH2:19]=O>C(O)(=O)C>[CH3:16][N:17]([CH2:19][C:12]1[O:13][C:7]2[CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:14])[F:15])[CH2:10][CH2:9][C:8]=2[CH:11]=1)[CH3:18]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000551-(4,7-Dihydrofuro[2,3-c]pyridin-6(5H)-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 19600081HCID 19600081, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.722 g (3.294 mmol) of 6-trifluoroacetyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 50 ml of acetic acid, 0.36 g (4.0 mmol) of 50% aqueous dimethylamine and 0.32 g (4.0 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1.5 hours. After the solvent was distilled off under reduced pressure, the residue was diluted with water, gently poured into ice-cooled aqueous sodium hydrogen carbonate, and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with water
  3. additiongently poured into ice-
  4. temperaturecooled aqueous sodium hydrogen carbonate
  5. extractionextracted with dichloromethane 3 times
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-51cceb0046044a97a1cf15140e9d3a6f
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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