1-Piperazinecarboxylic acid, ethyl ester → HCID 22047956, compound

HRID 638537Notes

Reaction equation

HRID 638537 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.CC[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:19]2[CH2:20][CH2:21][N:16]([C:14]([OH:15])=[O:13])[CH2:17][CH2:18]2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 14798Sodium HydroxideHCID 699943-Methoxybenzyl chloride

Product 1

HCID 22047956HCID 22047956, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 48.6 g (0.31 moles) of m-methoxybenzyl chloride, 49.0 g (0.31 moles) of ethyl N-piperazinocarboxylate, 250 ml of isopropyl alcohol and 35 ml of 10N sodium hydroxide was heated at reflux for 18 hours. The reaction mixture was evaporated in vacuo and gave an oil. The oil was Kugelrohr distilled bp 106° C./0.025 mm of mercury and gave 87.3 g of 4-[(3-methoxyphenyl)methyl]-1-piperazinecarboxylic acid, ethyl ether as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. customgave an oil
  5. distillationdistilled bp 106° C./0.025 mm of mercury

Sources & evidence

ORD record
ord-b986a627c4f14b0280f68aafcb9e72ca
Source dataset
uspto-grants-1985_12
Patent number
US04562189

Reaction notes

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