1-(2-Methoxyphenyl)piperazine → 3-[4-(2-Methoxyphenyl)piperazinyl]-2-phenylpropionic acid

HRID 1649867Notes

Reaction equation

HRID 1649867 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:15]([OH:25])(=[O:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH2:17]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:25])=[O:24])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 68114Atropic acid

Product 1

HCID 100886143-[4-(2-Methoxyphenyl)piperazinyl]-2-phenylpropionic acidYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Methoxyphenyl)piperazine (22.6 g, 0.118 mol) and atropic acid (174 g, 0.118 mol) in ethanol (300 ml) were heated under reflux for 18 hours, cooled to room temperature, and evaporated in vacuo. The solid was triturated with acetone (3×100 ml) to give a first crop of α-[1-[4-(2-methoxyphenyl)piperazinyl]methyl]phenyl acetic acid (13.8 g) as white crystals. The filtrate was evaporated in vacuo to give an oil which slowly crystallized over a one month period of time. The solid was triturated with acetone (200 ml) to give a second crop of the hemihydrate of the α-[1-[4-(2-methoxyphenyl)piperazinyl]methyl]phenylacetic acid (9.01 g) as white crystals, m.p. 160°-163° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. customevaporated in vacuo
  3. customThe solid was triturated with acetone (3×100 ml)

Sources & evidence

ORD record
ord-1243d81e4af74605b3cfcd75480dad24
Source dataset
uspto-grants-1990_05
Patent number
US04921958

Reaction notes

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