Trifluoroacetic acid → 3-[2-(2-Fluoro-5-bromobenzyloxy)ethyl]piperidine
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][CH2:22][O:23][CH2:24][C:25]2[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[F:32][C:26]1[CH:27]=[CH:28][C:29]([Br:31])=[CH:30][C:25]=1[CH2:24][O:23][CH2:22][CH2:21][CH:17]1[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 1-ml round bottom flask 1-(t-butoxycarbonyl)-3-[2-(2-fluoro-5-bromobenzyloxy)ethyl]piperidine (0.495 g) was dissolved in methylene chloride (4 ml) under a nitrogen atmosphere. The solution was cooled to 0° C. and trifluoroacetic acid (1 ml) was slowly added dropwise. The resulting mixture was stirred for thirty minutes at ambient temperature. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The resulting residue was used as is.
Workup
- customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
- extractionThe aqueous fraction was back extracted with methylene chloride
- dry with materialdried over sodium sulfate
- customThe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-66e0ef759dcc42a28d4664241a88bf9b
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245761B1
Reaction notes
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