Piperazine → 1-[(4-Bromophenyl)methyl]piperazine

HRID 1406633Notes

Reaction equation

HRID 1406633 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 685274-Bromobenzyl bromide

Product 1

HCID 8764941-[(4-Bromophenyl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-bromobenzyl bromide (4{9}, 7 g, 28.0 mmol, 1 equiv.), piperazine (14.5 g, 168.0 mmol, 6 equiv.), THF (61.2 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{9} (6.73 g, 94%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 7.42 (d, 2H, J=8.4 Hz) 7.19 (d, 2H, J=8.4 Hz), 3.42 (s, 2H) 2.87 (t, 4H, J=4.8 Hz), 2.38 (br s, 4H), 2.07 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 137.1, 131.3, 130.9, 120.8, 62.8, 54.2, 45.9.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{9} (6.73 g, 94%) as a white solid

Sources & evidence

ORD record
ord-36fbd88bc78843baa2d93aa8c6aab1cc
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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