1-(4-Fluorophenyl)piperazine → HCID 13073853, compound

HRID 463302Notes

Reaction equation

HRID 463302 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:14]1([CH2:17][Cl:18])[CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>C(O)C>[ClH:18].[ClH:18].[CH:14]1([CH2:17][N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium Bicarbonate

Product 1

HCID 13073853HCID 13073853, compoundYield 139.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 50 ml of ethanol, are added 3.6 g (0.02 mole) of 1-(4-fluorophenyl)piperazine, 2.0 g (0.022 mole) of cyclopropylmethyl chloride, and 1.9 g (0.023 mole) of sodium bicarbonate. The mixture is kept refluxing for 7 hours while being stirred. After having been cooled, the reaction mixture is freed from inorganic matters by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in diethyl ether and gaseous hydrogen chloride is introduced into the solution, while being cooled, to precipitate crystals which are collected by filtration. Upon recrystallization from ethanol there are obtained 4.7 g (77% yield) of 1-(cyclopropylmethyl)-4-(4-fluorophenyl)piperazine dihydrochloride melting at 153°-154° C.

Workup

  1. temperatureThe mixture is kept refluxing for 7 hours
  2. temperatureAfter having been cooled
  3. filtrationthe reaction mixture is freed from inorganic matters by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in diethyl ether
  6. additiongaseous hydrogen chloride is introduced into the solution
  7. temperaturewhile being cooled
  8. customto precipitate crystals which
  9. filtrationare collected by filtration
  10. customUpon recrystallization from ethanol

Sources & evidence

ORD record
ord-29c73aadd0bd43c9a8f078aab1435bb0
Source dataset
uspto-grants-1985_05
Patent number
US04518712

Reaction notes

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