Piperidine → 1-(But-3-yn-1-yl)piperidine
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][CH2:15][C:16]#[CH:17]>C(#N)C.O>[CH2:17]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:16][C:15]#[CH:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of piperidine (T1, 2.90 g, 34.0 mmol), potassium carbonate (3.00 g, 21.7 mmol), and 4-bromobut-1-yne (5.00 g, 37.6 mmol) in anhydrous acetonitrile (60 mL) was heated to 80° C. under nitrogen for 20 h. After this time, the reaction mixture was cooled to room temperature and diluted with water (50 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford compound T2 as light brown oil (1.89 g, 40%): MS (M+H) 138.
Workup
- temperatureAfter this time, the reaction mixture was cooled to room temperature
- extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
- dry with materialThe combined extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-44db4023ee7d40b187ef8c09aec1667f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416141B2
Reaction notes
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