Benzyl Chloride → (R)-1-Benzyl-3-methylpiperazine

HRID 1951738Notes

Reaction equation

HRID 1951738 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.[OH-].[Na+]>[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

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 6923226(R)-1-Benzyl-3-methylpiperazineYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1.0 g (10 mmol) (R)-2-methylpiperazine, 1.3 g (10 mmol) benzyl chloride and 4.1 g (30 mmol) potassium carbonate in 10 ml ethanol was heated at reflux over night. After cooling to room temperature the reaction mixture was diluted with a 0.5 M aqueous solution of sodium hydroxide and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. Flash column chromatography gave 0.93 g (49%) of the title compound as an off-white solid. MS m/e (%): 191 (M+H+, 100)

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. extractionextracted with three portions of dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb47dae0217b480a83c0b6e5ccfe3434
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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