Allyl bromide → Ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylate

HRID 2036144Notes

Reaction equation

HRID 2036144 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:16]([N:6]1[C@H:5]([CH3:8])[CH2:4][N:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:2]([CH3:1])[CH2:7]1)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 10607598Ethyl trans-2,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 10823138Ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl trans-2,5-dimethyl-1-piperazinecarboxylate (643 g, 3.45 mol), allyl bromide (328 mL, 3.80 mol), and sodium carbonate (440 g, 4.15 mol) in 2500 mL of acetonitrile was heated at reflux for 1.5 hours. The reaction was cooled to room temperature, filtered, and the solvent removed under vacuum. The residue was dissolved in 4000 mL of dichloromethane and washed with two 500 mL portions of 1 M sodium hydroxide. The dichloromethane solution was dried over magnesium sulfate and the solvent was removed to give 630 g (81%) of ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylate as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationfiltered
  4. customthe solvent removed under vacuum
  5. dissolutionThe residue was dissolved in 4000 mL of dichloromethane
  6. washwashed with two 500 mL portions of 1 M sodium hydroxide
  7. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-931f9dae6ba54580ba6aac316614491c
Source dataset
uspto-grants-2013_11
Patent number
US08575169B2

Reaction notes

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