Sodium Hydroxide → 1,4-Dibenzylpiperazine-2-carboxylic acid

HRID 1713491Notes

Reaction equation

HRID 1713491 reaction equation
Cl.Cl.[C:3]1([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH:11]2[C:23]([O:25]CC)=[O:24])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[C:3]1([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:12][CH:11]2[C:23]([OH:25])=[O:24])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68419710Ethyl 1,4-dibenzylpiperazine-2-carboxylate dihydrochloride

Product 1

HCID 223242451,4-Dibenzylpiperazine-2-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 1,4-bis(phenylmethyl)-2-piperazine carboxylate dihydrochloride (21 g, 52 mmol) were added ethanol (300 mL) and a 1 M aqueous sodium hydroxide solution (300 mL, 0.30 mmol), and the mixture was stirred at 80° C. for 3 hours. The reaction solution was concentrated, and then 1 M hydrochloric acid was added thereto until the pH was adjusted to 5. The reaction solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the resulting crystals was added diethyl ether, collected by filtration, and washed with diethyl ether to obtain the title compound (12 g, yield 76%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. addition1 M hydrochloric acid was added
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting crystals was added diethyl ether
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f04e8b7c5e5e44ffa385461a767067a2
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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