Trifluoroacetic acid → 4-(4-Ethynyl-1,3-thiazol-2-yl)piperidine
Reaction equation
[C:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[S:6][CH:7]=1)#[CH:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[S:6][CH:7]=1)#[CH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.87 g, 6.40 mmol) in anhydrous dichloromethane (16 ml) was added at 0° C. trifluoroacetic acid (16 ml). After stirring at 0° C. for 30 mins, the mixture was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was concentrated to dryness. The residue was washed with dichloromethane (extracted from solid phase) and the washing solution was concentrated to give 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine (1.176 g, yield 98%) as a white solid.
Workup
- concentrationthe mixture was concentrated under reduced pressure
- additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
- concentrationthe mixture was concentrated to dryness
- washThe residue was washed with dichloromethane (extracted from solid phase)
- concentrationthe washing solution was concentrated
Sources & evidence
- ORD record
- ord-63a081dddd814109a91eefcabe8084a6
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999989B2
Reaction notes
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