1-Bromo-3-chloropropane → 1-(3-Fluorophenyl)piperazine

HRID 1583540Notes

Reaction equation

HRID 1583540 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.[Cl:5][CH2:4][CH2:3][CH2:2][N:16]1[CH2:15][CH2:14][N:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 774181-(3-Fluorophenyl)piperazine

Product 2

HCID 774181-(3-Fluorophenyl)piperazineHCID 13312914HCID 13312914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 1-(3-chloropropyl)-4-(3-fluorophenyl piperazine used is prepared in the following manner: 32 g (203 m. moles) of 1-bromo-3-chloropropane are added drop by drop to a mixture of 12.2 g (67.7 m. moles) Of 1-(3-fluorophenyl piperazine [prepared according to D. R. Maxwell and W. R. Wragg, English Pat. No. 943,739, C.A. 60, 5522c (1964)], 9.4 g (68 m. moles) of potassium carbonate and 135 cc of N,N-dimethylformamide. The stirring is continued for 9 hours at ambient temperature. The inorganic products are then removed by filtration, then the filtrate is concentrated under reduced pressure. The residue is dissolved in ether, the solution washed with a saturated solution of sodium chloride, then dried on sodium sulfate. The evaporation of the ether supplies an oil which is distilled (boiling1 =137°-140°). The 1-(3-chloropropyl)-4-(3-fluorophenyl)piperazine is obtained in the form of an oil that is crystallized in hexane. Yield: 11.6 g (67%), Melting point=48°-49° C.

Workup

  1. customprepared
  2. customThe inorganic products are then removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in ether
  5. washthe solution washed with a saturated solution of sodium chloride
  6. customdried on sodium sulfate
  7. customThe evaporation of the ether
  8. distillationis distilled (boiling1 =137°-140°)

Sources & evidence

ORD record
ord-1af4e7bb1b3e4c1ea1208ccd2d76947c
Source dataset
uspto-grants-1985_11
Patent number
US04552878

Reaction notes

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