p-Bromobenzyl chloride → HCID 57849511, compound

HRID 737085Notes

Reaction equation

[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>C(#N)C>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:11]2[CH2:10][CH2:9][NH:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2 g of 2-phenylpiperazine were dissolved in acetonitrile and cooled to 0° C. A solution of 0.5 quiv. 4-bromobenzylchloride in acetonitrile was added dropwise over 1 h. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was purified by column chromatography (silica, eluent dichloromethane, 0-5% methanol) to afford 1 g of 1-(4-bromo-benzyl)-3-phenyl-piperazine. ES MS (+) m/z 301.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by column chromatography (silica, eluent dichloromethane, 0-5% methanol)

Sources & evidence

ORD record: ord-a62b97cd358e4cdc8116f7b345b6d4c2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595397B2

Reaction notes

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