Dimethylamine → 5-benzyl-2-dimethylaminomethyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

HRID 611427Notes

Reaction equation

HRID 611427 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][CH:15]=[CH:16][C:10]=2[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][NH:19][CH3:20].[CH2:21]=O>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][C:15]([CH2:18][N:19]([CH3:21])[CH3:20])=[CH:16][C:10]=2[C:9]1=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196002565-benzyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Product 1

HCID 196001075-benzyl-2-dimethylaminomethyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.181 g (0.796 mmol) of 5-benzyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one in 10 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 refluxing for 6 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 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. temperatureby refluxing for 6 hours
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate 3 times
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-a847527738a8452599752c97ffd9a1e8
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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