Benzyl Bromide → (S)-1-Benzyl-3-methylpiperazine

HRID 1057399Notes

Reaction equation

HRID 1057399 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:8]([N:6]1[CH2:5][CH2:4][NH:3][C@@H:2]([CH3:1])[CH2:7]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 6923224(S)-1-Benzyl-3-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-(+)-2-Methylpiperazine (2.63 g), benzylbromide (3.12 ml) and potassium carbonate (5.4 g) were heated together in acetonitrile (120 ml) at 40° C. for 3 days. The mixture was evaporated to dryness in vacuo and the residue partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was separated, dried (magnesium sulphate) and evaporated to dryness in vacuo. The residue was purified by column chromatography over silica gel using gradient elution (95/510 to 92/7/1 dichloromethane/methanol/ammonium hydroxide) to afford the title compound as a solid, 1.12 g.

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. customthe residue partitioned between aqueous sodium bicarbonate solution and ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by column chromatography over silica gel using gradient elution (95/510 to 92/7/1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-60f18218af7c44e1bd2bc66e0d33e391
Source dataset
uspto-grants-2003_02
Patent number
US06514975B1

Reaction notes

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