1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

HRID 654097Notes

Reaction equation

HRID 654097 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:5][CH2:4][CH2:3][CH2:2][N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine can be obtained as follows: a solution of 1-bromo-3-chloropropane (68 cc) and 4-(4-fluorophenyl)piperazine (50 g) in acetonitrile (400 cc) is stirred at 25° C. for 20 hours with potassium carbonate (97 g). The mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 9-cm diameter, 60-cm height) and eluted with ethyl acetate, 500-cc fractions being collected. Fractions 5 to 7 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine (44.4 g) in the form of a yellow oil.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 9-cm diameter, 60-cm height)
  4. washeluted with ethyl acetate, 500-cc fractions
  5. custombeing collected
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-bb410870684f46499c858dc0db3fca46
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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