Piperazine → 1-(4-Methylbenzyl)piperazine

HRID 1406640

Reaction equation

HRID 1406640 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1>[CH3:1][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 77224-Methylbenzyl chloride

Product 1

HCID 7647231-(4-Methylbenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-methylbenzyl chloride (4{13}, 6.1 mL, 46.2 mmol, 1 equiv.), piperazine (23.9 g, 277.4 mmol, 6 equiv.), THF (100.9 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{13} (6.56 g, 96%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.18 (d, 2H, J=8.0 Hz), 7.09 (d, 2H, J=7.5 Hz), 3.42 (s, 2H), 2.84 (t, 4H, J=5.0 Hz), 2.37 (br s, 4H), 2.31 (s, 3H), 1.54 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 136.3, 134.7, 129.0, 128.6, 63.2, 54.3, 45.9, 20.9.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{13} (6.56 g, 96%) as a white solid

Sources & evidence

ORD record
ord-99f40f9049de4c8bab3aea570c8409fb
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Linked notes

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