1-(4-Bromophenyl)piperazine → 2-(Methylamino)-2-oxoethyl 4-(4-bromophenyl)-1-piperazinecarboxylate

HRID 2246197Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14](=O)([O:21]C1C=CC([N+]([O-])=O)=CC=1)[O:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18]>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[O:21])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

1.17 g (4.85 mmol) of 1-(4-bromophenyl)piperazine are added to a solution of 1.47 g (4 mmol) of 2-(methyl-amino)-2-oxoethyl 4-nitrophenyl carbonate, obtained in step 2.1., in 18 ml of 1,2-dichloroethane. This reaction mixture is heated at 65° C. for 2.25 hours. The mixture is allowed to cool to room temperature and it is then concentrated under reduced pressure. The oily yellow residue is taken up in dichloromethane and washed successively with sodium hydroxide (1N), water, aqueous 5% citric acid solution, water and then brine. This organic phase is dried over sodium sulfate and is concentrated under reduced pressure. After washing with diisopropyl ether, 1.3 g of product are obtained in the form of a white solid.

Workup

customobtained in step 2.1
temperatureto cool to room temperature
concentrationit is then concentrated under reduced pressure
washwashed successively with sodium hydroxide (1N), water, aqueous 5% citric acid solution, water
dry with materialThis organic phase is dried over sodium sulfate
concentrationis concentrated under reduced pressure
washAfter washing with diisopropyl ether, 1.3 g of product
customare obtained in the form of a white solid

Sources & evidence

ORD record: ord-be197a490e4b4ec0892f48dfc7d56ea0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687503B2

Reaction notes

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