Piperazine → 1-[(3,4,5-Trimethoxyphenyl)methyl]piperazine

HRID 1406646Notes

Reaction equation

HRID 1406646 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6]Cl.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzene

Product 1

HCID 1040951-[(3,4,5-Trimethoxyphenyl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 3,4,5-trimethoxybenzyl chloride (4{16}, 5 g, 23.1 mmol, 1 equiv.), piperazine (11.9 g, 138.5 mmol, 6 equiv.), THF (50.5 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{16} (5.59 g, 91%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 6.46 (s, 2H), 3.75 (s, 6H), 3.72 (s, 3H), 3.30 (s, 2H), 2.78 (t, 4H, J=5.0 Hz), 2.29 (br s, 4H), 1.55 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 152.7, 136.4, 133.7, 105.4, 63.6, 60.5, 55.7, 54.2, 45.8.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{16} (5.59 g, 91%) as a white solid

Sources & evidence

ORD record
ord-2ab0ebd713674afc8cbabb3931f78891
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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