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

HRID 2393307Notes

Reaction equation

HRID 2393307 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 1M 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 1M sodium hydroxide
  7. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-f2125fb27290405eacfc81422c565fa9
Source dataset
uspto-grants-1998_09
Patent number
US05807858

Reaction notes

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