Sodium Bicarbonate → HCID 13231125, compound

HRID 905029Notes

Reaction equation

HRID 905029 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][CH2:12]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17]([NH:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:18])[CH3:15].C(=O)([O-])O.[Na+]>C(O)C>[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][N:23]1[CH2:22][CH2:21][N:20]([NH:19][C:17]([O:16][CH2:14][CH3:15])=[O:18])[CH2:25][CH2:24]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 111840715-bromo-1-phenyl-1-pentanoneHCID 13200156Ethyl piperazin-1-ylcarbamate

Product 1

HCID 13231125HCID 13231125, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.0 g of 1-benzoyl-4-bromobutane, 13.4 g of 1-(ethoxycarbonylamino)piperazine and 17.8 g of sodium hydrogen carbonate were heated under reflux in ethanol for 6 hours with stirring. The insoluble materials were removed from the reaction mixture by filtration. The solvent was distilled off, and water was added to the residue. The mixture was extracted with benzene. The extract was recrystallized from benzene-hexane to give 21.4 g of 4-(4-benzoylbutyl)-1-(ethoxycarbonylamino)-piperazine having a melting point of 105° to 106° C.

Workup

  1. customThe insoluble materials were removed from the reaction mixture by filtration
  2. distillationThe solvent was distilled off
  3. additionwater was added to the residue
  4. extractionThe mixture was extracted with benzene
  5. customThe extract was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-6ade663aa5af422791a2999fdf531c7d
Source dataset
uspto-grants-1983_12
Patent number
US04421754

Reaction notes

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