Piperazine → HCID 4020459, compound

HRID 1406667Notes

Reaction equation

HRID 1406667 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1>[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 114264722-Iodobenzyl Bromide

Product 1

HCID 4020459HCID 4020459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 2-iodobenzyl bromide (4{27}, 4.92 g, 16.8 mmol, 1 equiv.), piperazine (8.70 g, 101.0 mmol, 6 equiv.), THF (36.7 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{27} (4.43 g, 89%) as a light yellow liquid. 1H-NMR (400 MHz, CDCl3): δ 7.80 (dd, 1H, J=1.2, 8.0 Hz) 7.39 (dd, 1H, J=1.2, 7.6 Hz), 7.30-7.26 (m, 1H), 6.91 (dt, 1H, J=1.2, 7.2 Hz), 3.47 (s, 2H), 2.86 (t, 4H, J=4.8 Hz), 2.46 (br s, 4H), 1.76 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 140.4, 139.3, 130.2, 128.6, 127.8, 100.6, 66.9, 54.3, 46.0.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{27} (4.43 g, 89%) as a light yellow liquid

Sources & evidence

ORD record
ord-6cd659b5576c4c20815b4f8d2923e651
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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