Potassium Carbonate → 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazin-2-one

HRID 1466140Notes

Reaction equation

HRID 1466140 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]3=[O:18])[CH:7]=[CH:6][C:5]=12.I[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=4)[CH2:14][C:13]3=[O:18])[CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113464461-(2-Iodoethyl)-4-nitrobenzeneHCID 895261841-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-2-piperazinone

Product 1

HCID 895334871-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]piperazin-2-one (20 mg, 0.081 mmol) in DMF (1 mL) was added 1-(2-Iodoethyl)-4-nitrobenzene (27 mg, 0.097 mmol) and K2CO3 (45 mg, 0.32 mmol). The mixture was allowed to stir at RT for 16 hours. LC showed product formation. The desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 396 [M+1]+.

Workup

  1. customThe desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA)

Sources & evidence

ORD record
ord-30debf0cfe1a4600a3ddf32af340f3eb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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