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

HRID 429496Notes

Reaction equation

HRID 429496 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 1 M 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-piperazinecaboxylate.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturehours, cool the reaction mixture
  4. customevaporate in vacuo
  5. customto give a residue
  6. extractionextract with a 1 M 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-66f5d49a9def44e4b6461c0b936e6a3c
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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