1-Piperazinecarboxylic acid, ethyl ester → HCID 27267238, compound

HRID 638536Notes

Reaction equation

HRID 638536 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Cl.[CH3:11][CH2:12][O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15].[OH-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4][N:19]1[CH2:18][CH2:17][N:16]([C:14]([O:13][CH2:12][CH3:11])=[O:15])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 14798Sodium HydroxideHCID 748322,6-Dichlorobenzyl chloride

Product 1

HCID 27267238HCID 27267238, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 95.9 g (0.49 moles) of 2,6-dichlorobenzyl chloride, 77.6 g (0.49 moles) of ethyl N-piperazinocarboxylate, 500 ml of isopropyl alcohol and 70 ml of 10N sodium hydroxide was heated at reflux for 18 hours. The solution was evaporated in vacuo and gave a crystalline residue. The residue in 100 ml of water was extracted twice with 200 ml portions of dichloromethane. The combined organic extract was dried over anhydrous sodium sulfate, filtered, evaporated in vacuo and gave an oil. The oil was subjected to Kugelrohr distillation, bp 117° C./0.45 mm of mercury and gave 136.4 g of 4-(2,6-dichlorobenzyl)-1-piperazinecarboxylic acid, ethyl ester as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solution was evaporated in vacuo
  4. customgave a crystalline residue
  5. extractionThe residue in 100 ml of water was extracted twice with 200 ml portions of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customgave an oil
  11. distillationThe oil was subjected to Kugelrohr distillation, bp 117° C./0.45 mm of mercury

Sources & evidence

ORD record
ord-50e56a3d0dc643228245c5fe18449309
Source dataset
uspto-grants-1985_12
Patent number
US04562189

Reaction notes

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