Bromoacetyl bromide → (+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazine

HRID 362539Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:8]1)=[O:6].CCN(C(C)C)C(C)C.[Br:34][CH2:35][C:36](Br)=[O:37]>C(Cl)Cl>[Br:34][CH2:35][C:36]([N:10]1[CH2:11][CH2:12][N:7]([C:5](=[O:6])[C:4]2[CH:21]=[C:22]([CH3:24])[CH:23]=[C:2]([CH3:1])[CH:3]=2)[CH2:8][CH:9]1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)=[O:37]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of (+,-)-[3,5-dimethylbenzoyl]-3-(3,4-dichlorophenyl)piperazine (11.5 g, 31.65 mmol) in CH2Cl2 (200 mL) at 0° C. was added Hunig's base (4.5 g, 35 mmol) and bromoacetyl bromide (6.4 g, 31.65 mmol). The solution was stirred at 0° C. overnight under N2. After completion the reaction was diluted with CH2Cl2 (400 mL) and washed with brine (300 mL, 2×), dried over MgSO4, filtered and concentrated. The crude material was purified by flash grade silica gel chromatography, eluting with 2% [NH4OH/MeOH (1:9)]/98% CH2Cl2 to give the title compound as a light yellow solid (7.1 g, 47.3%), m.p. 77°-79° C., FAB MS [M+1]+ 35 Cl, 79Br 482.9, 484.9.

Workup

washwashed with brine (300 mL, 2×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by flash grade silica gel chromatography
washeluting with 2% [NH4OH/MeOH (1:9)]/98% CH2Cl2

Sources & evidence

ORD record: ord-98185fac8ad14c8fb692e9e31d8a7ca0
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869488

Reaction notes

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