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

HRID 485948

Reaction equation

HRID 485948 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.Cl.[OH-].[Na+]>C(O)(C)C>[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 313Hydrochloric AcidHCID 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 3776IsopropanolSolvent

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 isopropanol was refluxed for 48 hr. The reaction mixture was allowed to stand in a refrigerator overnight and filtered. The filtrate was treated with ethereal hydrogen chloride and the salt precipitated by the addition of ether. The white crystalline solid formed was dissolved in 0.1 mole of hydrochloric acid and then neutralized with sodium hydroxide producing a crystalline precipitate. This was recrystallized with isopropanol yielding 36 g. of the free base of the product which melted at 100°-101.5° C.

Workup

  1. additionA mixture of 35.1 g
  2. customto stand in a refrigerator overnight
  3. filtrationfiltered
  4. additionThe filtrate was treated with ethereal hydrogen chloride
  5. customthe salt precipitated by the addition of ether
  6. customThe white crystalline solid formed
  7. customThis was recrystallized with isopropanol yielding 36 g

Sources & evidence

ORD record
ord-380f4295623941fc9742303735cd2793
Source dataset
uspto-grants-1985_08
Patent number
US04538001

Linked notes

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