Isopropanol → 1-(o-Chlorophenoxy)-4-(4-phenyl-1-piperazinyl)-2-butanol

HRID 1639075Notes

Reaction equation

HRID 1639075 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH:5](Cl)[CH:6]([OH:9])[CH2:7][CH3:8].[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(O)C.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][CH:6]([OH:9])[CH2:7][CH2:8][N:24]1[CH2:25][CH2:26][N:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 70961-PhenylpiperazineHCID 14798Sodium HydroxideHCID 198402391-(o-Chlorophenoxy)-2-hydroxybutyl chloride

Product 1

HCID 131204511-(o-Chlorophenoxy)-4-(4-phenyl-1-piperazinyl)-2-butanol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 35.1 g (0.15 mole) of 1-(o-chlorophenoxy)-2-hydroxybutyl chloride, 32.6 g (0.2 mole) of N-phenylpiperazine and 400 ml of 2-propanol was heated at reflux for 48 hr. The resulting reaction mixture was allowed to stand in a refrigerator overnight and filtered. The filtrate was treated with ethereal hydrogen chloride and precipitated with ether. Upon filtering, a white crystalline solid formed which was dissolved in dilute hydrochloric acid and the mixture was then neutralized with aqueous sodium hydroxide producing a crystalline precipitate. This was recrystallized with isopropanol yielding 36 g of the free base, m.p. 100°-101.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hr
  3. customThe resulting reaction mixture
  4. customto stand in a refrigerator overnight
  5. filtrationfiltered
  6. additionThe filtrate was treated with ethereal hydrogen chloride
  7. customprecipitated with ether
  8. filtrationUpon filtering
  9. customa white crystalline solid formed which
  10. customThis was recrystallized with isopropanol yielding 36 g of the free base, m.p. 100°-101.5° C.

Sources & evidence

ORD record
ord-633d4877f7c74007851f781356d8dbb4
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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