4-Nitro-3-trifluoromethylphenol → Tert-butyl 4-(3-(4-nitro-3-(trifluoromethyl)phenoxy)propyl)piperazine-1-carboxylate

HRID 415076

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].CS(O[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25][CH2:24]2)=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14])([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A 100 mL flask was charged with 4-nitro-3-(trifluoromethyl)phenol (commercially available from Acros; 0.31 g, 1.8 mmol), tert-butyl 4-(3-(methylsulfonyloxy)propyl)-piperazine-1-carboxylate (0.64 g, 2.0 mmol), cesium carbonate (1.2 g, 3.6 mmol) and DMA. The reaction mixture was heated to 90° C. for 15 hours. The reaction mixture was allowed to cool to room temperature, extracted with ethyl acetate and 10% aqueous lithium chloride solution. The organic solvent was removed on a rotary evaporator under reduced pressure to yield tert-butyl 4-(3-(4-nitro-3-(trifluoromethyl)phenoxy)propyl)piperazine-1-carboxylate that was used without further purification. MS (EI): 434 (MH+).

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate and 10% aqueous lithium chloride solution
customThe organic solvent was removed on a rotary evaporator under reduced pressure

Sources & evidence

ORD record: ord-c06ef005cf0c432abf19a2828d100a5b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Linked notes

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