Dimethylamine → 2-(4-Benzyloxy-3-methoxy-phenyl)-1-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)ethane-1-one

HRID 611120Notes

Reaction equation

HRID 611120 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][C:21]3[CH:24]=[CH:25][O:26][C:20]=3[CH2:19]2)=[O:17])=[CH:11][C:10]=1[O:27][CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][NH:30][CH3:31].[CH2:32]=O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][C:21]3[CH:24]=[C:25]([CH2:29][N:30]([CH3:32])[CH3:31])[O:26][C:20]=3[CH2:19]2)=[O:17])=[CH:11][C:10]=1[O:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196001972-(4-benzyloxy-3-methoxyphenyl)-1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)ethan-1-one

Product 1

HCID 195999972-(4-Benzyloxy-3-methoxy-phenyl)-1-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)ethane-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.290 g (0.768 mmol) of 2-(4-benzyloxy-3-methoxyphenyl)-1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)ethan-1-one in 20 ml of acetic acid, 0.104 ml (1.15 mmol) of 50% aqueous dimethylamine and 0.094 ml (1.15 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 40 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1 to 25/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1 to 25/1)

Sources & evidence

ORD record
ord-4661598492f64e5ab33222ac992808a7
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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