Diethyl Ether → Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

HRID 1601445Notes

Reaction equation

HRID 1601445 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].C(OCC)C>C(O)C>[C:14]([CH2:15][CH2:16][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8821Ethyl AcrylateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 23000690Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine t-butyl 1-piperazinecarboxylate (10.47 g, 56.2 mmol), ethyl acrylate (8 mL) in ethanol (30 mL). Heat at reflux. After 5.5 hours, cool the reaction mixture and evaporate in vacuo to give a residue. Combine the residue and diethyl ether (200 mL) and extract with a 1M aqueous solution of hydrochloric acid. Adjust the pH of the aqueous layer to basic using sodium bicarbonate and then extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give t-butyl 4-carboethoxyethyl-1-piperazinecarboxylate.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturecool the reaction mixture
  4. customevaporate in vacuo
  5. customto give a residue
  6. extractionextract with a 1M aqueous solution of hydrochloric acid
  7. extractionextract with ethyl acetate
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-466b15e208934532bc0d7b85fd04cc96
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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