Sodium Chloride → HCID 21492253, compound

HRID 1973552Notes

Reaction equation

HRID 1973552 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.[OH-].[Na+].[Cl-].[Na+]>O.O1CCCC1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:14][CH2:13][CH2:12][O:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2697221-(4-Methoxyphenyl)piperazineHCID 129593811-(3-Bromopropoxy)naphthalene

Product 1

HCID 21492253HCID 21492253, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.6 g (40 mMol) 1-(naphth-1-yloxy)-3-bromopropane were mixed with 7.7 g (40 mMol) 1-(4-methoxyphenyl)-piperazine, 8.1 g (80 mMol) anhydrous triethylamine and 40 ml. anhydrous tetrahydrofuran and the reaction mixture subsequently maintained at reflux temperature for 10 hours. After cooling, the precipitated triethylamine hydrobromide was filtered off with suction. The filtrate was substantially evaporated in a vaccum, the residue was taken up in chloroform and the solution obtained was shaken with dilute aqueous sodium hydroxide solution, then with an aqueous solution of sodium chloride and thereafter with water. The organic phase was dried over anhydrous sodium sulfate, filtered through active charcoal and finally freed from chloroform in a vacuum. The oily residue was brought to crystallization by the addition of isopropanol. After recrystallization from methanol, with the addition of active charcoal, there were obtained 10.2 g (68% of theory) 1-(4-methoxyphenyl)-4-[3-(naphth-1-yloxy)-propyl]-piperazine, which had a melting point of 68° - 69° C. The corresponding hydrochloride was obtained by passing dry hydrogen chloride through a dioxan solution of the base. It had a melting point of 235° - 238° C.

Workup

  1. temperatureat reflux temperature for 10 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated triethylamine hydrobromide was filtered off with suction
  4. customThe filtrate was substantially evaporated in a vaccum
  5. customthe solution obtained
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered through active charcoal
  8. customThe oily residue was brought to crystallization by the addition of isopropanol
  9. customAfter recrystallization from methanol
  10. additionwith the addition of active charcoal

Sources & evidence

ORD record
ord-599610eb9ce84203a4b61e31924f90eb
Source dataset
uspto-grants-1976_12
Patent number
US03997667

Reaction notes

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