Piperazine → 1-(2,5-Dimethoxyphenyl)piperazine

HRID 2376676Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[O:16][CH3:17].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][O:14][C:12]1[CH:13]=[CH:8][C:9]([O:16][CH3:17])=[CH:10][C:11]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

1.98 g of piperazine, 1.0 g of 1-bromo-2,5-dimethoxybenzene, 800 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 310 mg of palladium(II) acetate and 2.25 g of cesium carbonate are dissolved in 30 ml of 1,4-dioxane and stirred at 100° C. under an argon atmosphere for 24 hours. The reaction mixture is extracted with 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution, and the combined aqueous phases are basified with 2N sodium hydroxide solution and extracted five times with 50 ml of dichloromethane each time. The combined organic phases are dried over MgSO4 and then the solvent is removed in vacuo. 500 mg of 1-(2,5-dimethoxyphenyl)piperazine are obtained as an amorphous solid.

Workup

extractionThe reaction mixture is extracted with 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution
extractionextracted five times with 50 ml of dichloromethane each time
dry with materialThe combined organic phases are dried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-7e195da5ae02465bbb10dd0110b8dee8
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468369B2

Reaction notes

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