Piperazine → 4-(Piperazinylmethyl)styrene

HRID 1406669Notes

Reaction equation

HRID 1406669 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1)=[CH2:2].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C1COCC1>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 33328804-(Piperazinylmethyl)styreneYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-vinylbenzyl chloride (7, 5.56 g, 32.8 mmol, 1 equiv.), piperazine (16.9 g, 196.6 mmol, 6 equiv.), THF (71.8 mL). Purification with flash column chromatography on silica gel (gradient, 4:1 to 1:4 EtOAc:MeOH) afforded 8 (5.39 g, 81%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.32 (d, 2H, J=8.0 Hz), 7.24 (d, 2H, J=8.0 Hz), 6.66 (dd, 1H, J=11.0, 18.0 Hz), 5.69 (dd, 1H, J=0.5, 18.0 Hz), 5.18 (dd, 1H, J=0.5, 11.0 Hz), 3.43 (s, 2H), 2.84 (t, 4H, J=5.0 Hz), 2.63 (br s, 1H), 2.37 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 137.5, 136.4, 136.2, 129.1, 125.8, 113.3, 63.1, 54.0, 45.7.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (gradient, 4:1 to 1:4 EtOAc:MeOH)

Sources & evidence

ORD record
ord-88b3ba311cf74ac180612be48ada0f4e
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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