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

HRID 704898Notes

Reaction equation

HRID 704898 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 (17.4 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 3-[4-(2-methoxyphenyl)piperazinyl]-2-phenylpropionic acid (13.8 g) as white crystals. The filtrate was evaporated in vacuo to give an oil which slowly crystallized over 1 month. The solid was triturated with acetone (200 mL) to give a second crop of the same hemihydrate product (9.01 g) as white crystals, mp. 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-242ebd3168df4d9fbc9edb78b61136f9
Source dataset
uspto-grants-1991_01
Patent number
US04988814

Reaction notes

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