Potassium Carbonate → 4-(4-Bromobenzyl)piperazine, N1-BOC protected

HRID 1711116Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][CH:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-Bromo-4-(bromomethyl)benzene (8.078 g, 32.3 mmol) and tert-butyl piperazine-1-carboxylate (6.625 g, 35.6 mmol) were dissolved in DMF (40 ml) and K2CO3 (8.93 g, 64.6 mmol) was added. The reaction mixture was heated to 60° C. for 4 h and then filtered through a pad of celite. The filtrate was evaporated and the residue was triturated in hexanes to produce compound 451 as white solid (9.46 g, 82% yield). LCMS: 255.0 (M+H)+.

Workup

filtrationfiltered through a pad of celite
customThe filtrate was evaporated
customthe residue was triturated in hexanes

Sources & evidence

ORD record: ord-0b6337a23d7745c6bc8c3ad9cca4363f
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790729B2

Reaction notes

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