Dimethylamine → 2-dimethylaminomethyl-5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16]3[O:19][CH:20]=[CH:21][C:15]=3[C:14]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)(=O)C>[CH3:23][N:24]([CH2:26][C:20]1[O:19][C:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:14](=[O:22])[C:15]=2[CH:21]=1)[CH3:25]Participants
5
Procedure
To a solution of 0.242 g (0.814 mmol) of 5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one in 10 ml of acetic acid, 0.37 g (4.1 mmol) of 50% aqueous dimethylamine and 0.33 g (4.1 mmol) of 37% aqueous formaldehyde were added, followed by overnight refluxing. 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
- temperaturerefluxing
- distillationAfter the solvent was distilled off under reduced pressure
- extractionextracted with ethyl acetate 3 times
- dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)
Sources & evidence
- ORD record
- ord-ee78eaa981214c4ba4ca988292073ab4
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998433
Reaction notes
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