Acrolein → HCID 22676614, compound
Reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]1[CH2:24][CH2:23][N:22]2C(=N[CH2:19][CH2:20][CH2:21]2)C[CH2:15]1.C(C=C)=O.[NH2:29][C:30]1C=NC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH-].[Na+]>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:30]=[N:29][CH:15]=[CH:14][CH:24]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
To a solution of 4-benzylpiperidine (3.51 g) in 40 ml of tetrahyfrofuran, 1,8-diazabicyclo[5.4.0]-7-undecene (0.03 ml) was added and the mixture was cooled at −20° C. Acrolein (1.485 ml) was added dropwise for 10 min and the mixture was stirred for 1 h at −20° C. 3-Aminopyridine (1.88 g) and sodium triacetoxyborohydride (8.48 g) were added and the mixture was stirred at room temperature for 15 h. 1N NaOH (120 ml) was added and stirred for 1 h. The reaction mixture was extracted with ethyl ether (60 ml) 3 times. The combined organic layer was washed with brine (50 ml), dried over anhydrous MgSO4. After concentration, the residue was purified on silica gel column chromatography (AcOEt-methanol 3:1) to give the title compound (2.34 g, yield 37.8%).
Workup
- stirringthe mixture was stirred at room temperature for 15 h
- stirringstirred for 1 h
- extractionThe reaction mixture was extracted with ethyl ether (60 ml) 3 times
- washThe combined organic layer was washed with brine (50 ml)
- dry with materialdried over anhydrous MgSO4
- concentrationAfter concentration
- customthe residue was purified on silica gel column chromatography (AcOEt-methanol 3:1)
Sources & evidence
- ORD record
- ord-db3c48d2cee942f68ed8948222d55e98
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562978B1
Reaction notes
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