Benzyl Bromide → 1-Benzyl-3-ethylpiperazine

HRID 1357604Notes

Reaction equation

HRID 1357604 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([CH:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1)[CH3:10]>CN(C=O)C>[CH2:1]([N:15]1[CH2:14][CH2:13][NH:12][CH:11]([CH2:9][CH3:10])[CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 140941882-Ethylpiperazine

Product 1

HCID 220365411-Benzyl-3-ethylpiperazineYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (38.7 g, 0.22 mol) was added in portions to a chilled (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M aqueous HCl. The aqueous phase was made alkaline (11 M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calcd, 76.42; found, 75.85.

Workup

  1. customdid not exceed 20° C
  2. customthe solvent was evaporated
  3. customthe residue was partitioned between CHCl3/0.5 M aqueous HCl
  4. extractionextracted three times with CHCl3
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe resulting oil was purified by column chromatography on silica

Sources & evidence

ORD record
ord-7c96d3ff2ad8418eaedd3d4ce60d4812
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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