1-(2-Methoxyphenyl)piperazine → 3-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

HRID 1413543Notes

Reaction equation

HRID 1413543 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.[CH2:15](Cl)[CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)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]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanol

Product 1

HCID 4109013-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-olYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

46 g of 1-(2-methoxyphenyl)-piperazine and 24.5 g of trimethylene chlorohydrine are dissolved in 200 ml of ethanol, and 25 g of potassium carbonate are added to the solution. The mixture is refluxed for 30 hours, thereafter it is cooled to 0° C., diluted with 50 ml of ethyl ether, filtered, and the filtrate is evaporated. The residue is dissolved in 100 ml of 50° C. benzene, the solution is cooled to 0° C., and allowed to stand for 10 hours. The separated crystals are filtered off and dried. 46 g (77%) of 3-[4-(2-methoxyphenyl)-piperazin-1-yl]-1-hydroxy-propane are obtained; m.p.: 92°-93° C.

Workup

  1. temperatureThe mixture is refluxed for 30 hours
  2. filtrationfiltered
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in 100 ml of 50° C. benzene
  5. temperaturethe solution is cooled to 0° C.
  6. filtrationThe separated crystals are filtered off
  7. customdried

Sources & evidence

ORD record
ord-e4f7f8efe83d49fb958cc503ac640cd3
Source dataset
uspto-grants-1981_02
Patent number
US04250310

Reaction notes

Loading…