Triethylamine → 1-[4-(Trifluoromethyl)benzene-1-sulfonyl]piperazine--hydrogen chloride (1/1)
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([S:29]([Cl:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[ClH:32].[F:34][C:22]([F:21])([F:33])[C:23]1[CH:24]=[CH:25][C:26]([S:29]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)(=[O:31])=[O:30])=[CH:27][CH:28]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-tert-butyloxycarbonylpiperazine (1.00 g, 5.37 mmol) in dichloromethane were added triethylamine (1.05 eq, 0.78 ml) and 4-(trifluoromethyl)-benzenesulfonyl chloride (1.02 eq, 1.345 g). The mixture was stirred overnight at room temperature, diluted with dichloromethane, washed with aqueous sodium bicarbonate solution, water, dried over magnesium sulfate and evaporated. The resulting white solid was dissolved in ethyl acetate and a 5 M solution of hydrogen chloride in ethyl acetate added dropwise. The mixture was stirred 3 h at 50° C. The precipitated solid was filtered and dried to afford the title compound (558 mg, 31%) which was used without further purification. MS (m/z): 295.4 (M+H)+.
Workup
- washwashed with aqueous sodium bicarbonate solution, water
- dry with materialdried over magnesium sulfate
- customevaporated
- dissolutionThe resulting white solid was dissolved in ethyl acetate
- additiona 5 M solution of hydrogen chloride in ethyl acetate added dropwise
- stirringThe mixture was stirred 3 h at 50° C
- filtrationThe precipitated solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-1c31bd3c5b534ffe8922bc3315a8f7d6
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507736B2
Reaction notes
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