Benzyl Bromide → (3r,5s)-1-Benzyl-3,5-dimethylpiperazine

HRID 500446Notes

Reaction equation

HRID 500446 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.C(=O)(O)[O-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([N:6]1[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazineYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (cis)-2,6-dimethylpiperazine (900 mg, 8.49 mmol) and sodium bicarbonate (0.2 ml of saturated solution) in THF (5 ml) was added benzyl bromide (1.02 ml, 8.49 mmol). The mixture was exposed to microwave irradiation at 80° C. for 15 minutes. The solvent was removed in vacuo and the residue was washed with sodium bicarbonate solution and extracted with dichloromethane. The residue was purified by flash chromatography eluting with 5-10% (v/v) methanol in dichloro-methane to afford 1-N-benzyl-(cis)-3,5-dimethylpiperazine as a clear oil (900 mg, 4.40 mmol).

Workup

  1. customirradiation at 80° C. for 15 minutes
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. customThe residue was purified by flash chromatography
  6. washeluting with 5-10% (v/v) methanol in dichloro-methane

Sources & evidence

ORD record
ord-0831377fd2064077964211892e15656a
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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