Trifluoroacetic acid → 1-[2-(7-Methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine
Reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]2[CH:33]=[N:32][C:31]3[C:26](=[CH:27][C:28]([O:34][CH3:35])=[CH:29][CH:30]=3)[N:25]=2)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[CH3:35][O:34][C:28]1[CH:27]=[C:26]2[C:31]([N:32]=[CH:33][C:24]([S:23][CH2:22][CH2:21][N:18]3[CH2:17][CH2:16][CH:15]([NH2:14])[CH2:20][CH2:19]3)=[N:25]2)=[CH:30][CH:29]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (5.41 mL, 70.2 mmol, 15.0 eq) is added at 0° C. to a stirred solution of {1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (2.0 g, 4.68 mmol, 1.0 eq) in dichloromethane (200 mL). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×50 mL) and water (50 mL) and the pH value adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine as an orange oil (1.40 g, 92% yield).
Workup
- extractionthe reaction mixture is extracted with dichloromethane (3×50 mL) and water (50 mL)
- additionthe pH value adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
- dry with materialThe combined organic layers are dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bdf3ce000ac340239756af9021c338b6
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716280B2
Reaction notes
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