Triethylamine → 1,4-Bis(phenylmethyl)-2-piperazinepropanoic acid

HRID 1031567Notes

Reaction equation

HRID 1031567 reaction equation
Br[CH:2]([CH2:8]Br)[C:3]([O:5]CC)=[O:4].[CH2:10]([NH:17][CH2:18][CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:28](N(CC)CC)[CH3:29]>C1C=CC=CC=1>[C:3]([CH2:2][CH2:8][CH:18]1[CH2:19][N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:29][CH2:28][N:17]1[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8793BenzathineHCID 97945Ethyl 2,3-dibromopropionate

Product 1

HCID 855762681,4-Bis(phenylmethyl)-2-piperazinepropanoic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 43.29 g (166.0 mmol) of ethyl 2,3-dibromopropionate in 145 ml of benzene warmed at 40° C. was added dropwise a solution of 40 g (166.0 mmol) of N,N'-dibenzylethylenediamine and 46.2 ml (166.0 mmol) of triethylamine in 40 ml of benzene. The vigourous stirred suspension was heated under reflux overnight, cooled and filtered. The benzene layer was washed three times with 50 ml of water. The organic layer was dried over magnesium sulfate. After evaporation 58.95 g of a thick oil was obtained which was purified by chromatography using dichloromethane/ethyl acetate (90:10) to yield 50.4 g (89.7%) of title compound.

Workup

  1. temperatureThe vigourous stirred suspension was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe benzene layer was washed three times with 50 ml of water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customAfter evaporation 58.95 g of a thick oil
  8. customwas obtained which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-d5fee9294d0c4534b1da7f5c38cbe0aa
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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