1-Propanol → 2-{1-[4-(2-Methoxyphenyl)piperazinyl]methyl}-3-benzenepropanoic acid

HRID 1769618Notes

Reaction equation

HRID 1769618 reaction equation
[C:1]1([CH2:7][C:8](=C)[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[CH2:27](O)CC>>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:2]2[C:1]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 13461-(2-Methoxyphenyl)piperazineHCID 3035712-Benzylacrylic Acid

Product 1

HCID 194335722-{1-[4-(2-Methoxyphenyl)piperazinyl]methyl}-3-benzenepropanoic acid

Procedure

2-(Phenylmethyl)propenoic acid (Mannich and Ganz, Chem. Ber., 1922, 55, 3486) (2.00 g, 12.35 mmol) and 1-(2-methoxyphenyl)piperazine (2.37 g, 12.35 mmol) in propanol (25 ml) were heated under reflux for 18 hours, cooled to room temperature, and evaporated in vacuo. The residue was triturated with acetone and ether to give the product (0.80 g) as a colourless powder, m.p. 155°-158°. (Found: C, 71.6; H, 7.4; N, 7.6. C21H26N2O3 requires C, 71.2; H, 7.3; N, 7.9%.)

Workup

  1. temperatureunder reflux for 18 hours
  2. customevaporated in vacuo
  3. customThe residue was triturated with acetone and ether

Sources & evidence

ORD record
ord-5d68411d09544da6821032811303fa9f
Source dataset
uspto-grants-1995_01
Patent number
US05382583

Reaction notes

Loading…