Ethyl Acetate → HCID 90020473, compound

HRID 2200152Notes

Reaction equation

HRID 2200152 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].CC1C=CC(S(O[CH2:31][CH2:32][F:33])(=O)=O)=CC=1.CCOC(C)=O>CN(C)C1C=CN=CC=1.C1COCC1>[F:33][CH2:32][CH2:31][N:17]1[CH2:18][CH2:19][N:14]([C:6]2[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 90020561HCID 90020561, compound

Product 1

HCID 90020473HCID 90020473, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Mix (3-nitro-5-(trifluoromethyl)phenyl)piperazine (200 mg, 0.73 mmol), 2-fluoroethyl 4-methylbenzenesulfonate (320 mg, 1.46 mmol) and 4-dimethylaminopyridine (50 mg, 0.37 mmol) in THF (15 mL), stir at 90° C. overnight. TLC (EtOAc:PE=1:1) shows the reaction is complete. Concentrate under reduced pressure to give a residue, purify the residue by flash chromatography (silica gel, PE:EtOAc=1:1) to yield a white solid as the target compound (120 mg, 51%).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customto give a residue
  3. custompurify the residue by flash chromatography (silica gel, PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-18d5e288570341bbbe73c53454b9b6fc
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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