Dimethylamine → N,N-dimethyl-[5-(3-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine
Reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[O:20][CH:21]=[CH:22][C:16]=2[CH2:15]1)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][NH:27][CH3:28].[CH2:29]=O>C(O)(=O)C>[CH3:26][N:27]([CH2:29][C:21]1[O:20][C:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C:11]3[CH:23]=[CH:24][CH:25]=[C:9]([C:1](=[O:8])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:10]=3)[CH2:15][C:16]=2[CH:22]=1)[CH3:28]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 0.200 g (0.604 mmol) of 5-(3-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.082 ml (0.91 mmol) of 50% aqueous dimethylamine and 0.073 ml (0.73 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 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
- distillationAfter the solvent was distilled off under reduced pressure
- extractionextracted with dichloromethane 2 times
- washThe combined organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- 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-fcdf1c67061e40e8a9a7aeb4751f941f
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998433
Reaction notes
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