Reaction equation
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH2:23]([NH:25][CH3:26])C.C=O.[C:29](O)(=O)[CH3:30]>>[CH2:29]([C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:8][CH2:9][C:4]=2[C:3]=1[CH2:23][NH:25][CH3:26])[CH3:30]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 0.400 g (1.345 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 0.14 ml (1.6 mmol) of N-Ethylmethylamine and 0.13 9 (1.6 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide 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
- distillationAfter the solvent was distilled off under reduced pressure
- extractionextracted with dichloromethane 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-6b244c45fd7d4ddeab8e414b0545dfed
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998433
Linked notes
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