Potassium Carbonate → 1-Benzyl-4-glycidylpiperazine

HRID 555303Notes

Reaction equation

HRID 555303 reaction equation
Br[CH2:2][CH:3]1[CH2:5][O:4]1.C([O-])([O-])=O.[K+].[K+].[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl.CO>C(#N)C>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH:3]2[CH2:5][O:4]2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 759941-BenzylpiperazineHCID 21226129Dichloromethane methanol

Product 1

HCID 111956421-Benzyl-4-glycidylpiperazineYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-bromomethyl-oxirane (2.3 mL, 27.5 mmol) in 40 mL of ACN are added K2CO3 (3.8 g, 27.5 mmol) and a solution of 1-benzyl-piperazine (5.81 g, 25 mmol) in 60 mL of ACN. After 24 hr at rt the reaction is judged to be completed by tlc monitoring (SiO2, DCM:MeOH 20:1). The reaction mixture is filtered off and the filtrate is concentrated in vacuo. Flash chromatography on a 7×15 cm2 column of SiO2 using DCM:MeOH (20:1) as eluting solvent and removal of the solvent gives the title compound (4.87 g, 84%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. washas eluting
  4. customsolvent and removal of the solvent

Sources & evidence

ORD record
ord-9b43ae3727164acd8584b82b3f94b560
Source dataset
uspto-grants-2011_11
Patent number
US08053436B1

Reaction notes

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