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

HRID 1769617Notes

Reaction equation

HRID 1769617 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 product (13.8 g) as white crystals. The filtrate was evaporated in vacuo to give an oil which slowly crystallised over 1 month. The solid was triturated with acetone (200 ml) to give a second crop of the hemihydrate of the product (9.01 g) as white crystals, m.p. 160°-163°. (Found: C, 68.4; H, 7.2; N, 7.9. C20H24N2O3.0.5H2O requires C, 68.8; H, 7.21 N, 8.0%.)

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-7af6436f29c943f9b8402025becc0293
Source dataset
uspto-grants-1995_01
Patent number
US05382583

Reaction notes

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