1-Phenylpiperazine → 1-Phenoxy-4-(4-phenyl-1-piperazinyl)-2-butanol

HRID 1382397Notes

Reaction equation

HRID 1382397 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][CH2:15][CH:16]([OH:25])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[O:18]([CH2:17][CH:16]([OH:25])[CH2:15][CH2:14][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 131203424-Chloro1-phenoxy-2-butanol

Product 1

HCID 144229031-Phenoxy-4-(4-phenyl-1-piperazinyl)-2-butanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6.5 g (0.04 mole) of 1-phenylpiperazine, 8.4 g (0.042 mole) of 4-chloro-1-phenoxy-2-butanol and 15.9 g (0.15 mole) of anhydrous sodium carbonate in 200 ml of 1-butanol was heated at reflux 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between water and benzene. The benzene layer was washed with water and aqueous saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure to give the title product in the residue which was recrystallized from isopropyl alcohol to give 8.9 g (68%) of white powder, m.p. 93°-94° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between water and benzene
  5. washThe benzene layer was washed with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-303220ce004d4fad8b1340743f36b87e
Source dataset
uspto-grants-1989_02
Patent number
US04806555

Reaction notes

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