5-(2-Bromoethyl)-2-benzofuran-1(3H)-one → 1,4-Bis[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one

HRID 1466146Notes

Reaction equation

HRID 1466146 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][C:14]3=[O:19])=[CH:10][C:5]=2[CH2:4][O:3]1.Br[CH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]2[C:27](=[O:30])[O:28][CH2:29][C:25]=2[CH:24]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][C:26]5[C:27](=[O:30])[O:28][CH2:29][C:25]=5[CH:24]=4)[CH2:15][C:14]3=[O:19])=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 675131635-(2-Bromoethyl)-2-benzofuran-1(3H)-oneHCID 1175993331-[2-(1,3-Dihydro-1-oxo-5-isobenzofuranyl)ethyl]-2-piperazinone

Product 1

HCID 895334791,4-Bis[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-[2-(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one (30 mg, 0.12 mmol) and 5-(2-Bromoethyl)-2-benzofuran-1(3H)-one (56 mg, 0.23 mmol) in DMF (2 ml) was added TEA (0.048 ml, 0.35 mmol) and tetrabutylammonium iodide (4.3 mg, 0.012 mmol). The mixture was heated to 55° C. for 16 hours. LC showed formation of the desired product, which was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 421 [M+1]+.

Sources & evidence

ORD record
ord-21c76461506a46b0a0487a8f880d9d7e
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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