Piperazine → 1-(4-isopropylbenzyl)piperazine

HRID 1406651Notes

Reaction equation

HRID 1406651 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C1COCC1>[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 749164-Isopropylbenzyl chloride

Product 1

HCID 25748441-(4-isopropylbenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-isopropylbenzyl chloride (4{19}, 5 g, 29.6 mmol, 1 equiv.), piperazine (15.3 g, 177.9 mmol, 6 equiv.), THF (64.9 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{19} (5.82 g, 90%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.21 (d, 2H, J=8.0 Hz), 7.14 (d, 2H, J=8.0 Hz), 4.15 (q, 2H, J=7.0 Hz), 3.43 (s, 2H), 2.89-2.84 (m, 5H), 2.39 (br s, 4H), 2.25 (br s, 1H), 1.22 (d, 6H, J=6.5 Hz). 13C-NMR (125 MHz, CDCl3): δ 147.3, 135.0, 128.9, 125.9, 63.2, 54.1, 45.7, 33.5, 23.8.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{19} (5.82 g, 90%) as a white solid

Sources & evidence

ORD record
ord-a9243f990569409086db95522e1eaf6a
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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