Methanol → 1-(4-Azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanone
Reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:20][CH2:19]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CO.C(OCC)C>C(Cl)Cl>[NH:14]1[CH2:15][CH:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])[CH2:22][CH2:23]2)[CH2:17]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-[4-(1-benzhydryl-azetidin-3-yl)-piperazin-1-yl]-2,2,2-trifluoro-ethanone (2.11 g, 5.23 mmol) in CH2Cl2 (60 mL) was added 1-chloroethyl chloroformate (2.0 mL, 18.35 mmol) at 0° C. under N2. The resulting mixture was stirred at 0° C. for 90 min and then methanol (4 mL) was added. The resulting mixture was refluxed for 1 h. Upon cooling, diethyl ether (50 mL) was added to the mixture. The resulting solid was collected by filtration and dried to yield the title compound, which was used in the next reaction without further purification. MS m/z (M+H+) 238.1.
Workup
- temperatureThe resulting mixture was refluxed for 1 h
- temperatureUpon cooling
- filtrationThe resulting solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-68586238c42340bf9a14e7599d4b9a63
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415341B2
Reaction notes
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