Piperidine → HCID 86638135, compound
Reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:12])=[CH:4][CH:3]=1Participants
5
Procedure
9 g (39 mmol) of 3-(6-bromo-pyridin-3-yl)-propionic acid, 22.5 g (195 mmol) of NEM and 12.83 g (39 mmol) of TOTU were dissolved in 30 ml of DMF and stirred at room temperature for 15 min. 3.33 g (39 mmol) of piperidine were, and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with a saturated sodium hydrogencarbonate solution. The organic phase was dried with sodium sulfate, filtered, and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography. Yield: 10.2 g.
Workup
- stirringthe reaction mixture was stirred at room temperature for 16 h
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washthe solution was washed with a saturated sodium hydrogencarbonate solution
- dry with materialThe organic phase was dried with sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-d257becf78ed4c05ac19c6aa0ee23374
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188291B2
Reaction notes
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