1-Bromo-3-chloropropane → HCID 70202671, compound

HRID 342595Notes

Reaction equation

HRID 342595 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[Br:19][CH2:20][CH2:21][CH2:22]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:19][CH2:20][CH2:21][CH2:22][N:14]1[CH2:15][CH2:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C:2]([F:1])([F:17])[F:18])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 104915651-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazine

Product 1

HCID 70202671HCID 70202671, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine (2.37 g, 9.1 mmol), 1-bromo-3-chloropropane (14.34 g, 9 mL, 91.1 mmol), potassium carbonate (1.88 g, 13.6 mmol) and acetonitrile (40 mL) was heated 16 hours at reflux under argon. The reaction mixture was allowed to cool to 25° C., then filtered and concentrated in vacuo. The residue was further concentrated at 60° C. in vacuo to remove excess 1-bromo-3-chloropropane. The residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give a mixture of 1-chloro- and 1-bromo-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane (1.4 g).

Workup

  1. temperaturewas heated 16 hours
  2. temperatureat reflux under argon
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationThe residue was further concentrated at 60° C. in vacuo
  6. customto remove excess 1-bromo-3-chloropropane
  7. customThe residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1)
  8. customto give

Sources & evidence

ORD record
ord-a60025a1d01445988e686a50e1b361a9
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

Loading…