1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazine

HRID 1975882Notes

Reaction equation

HRID 1975882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:16][CH2:17][Cl:18].C(N(CC)CC)C>>[Cl:18][CH2:17][CH2:16][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 8471TriethylamineHCID 936011-(3,4-Dichlorophenyl)piperazine

Product 1

HCID 120698951-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazineYield 35.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3,4-dichlorophenyl)-piperazine (0.05 mol), 1-bromo-2-chloroethane (0.1 mol) and triethylamine (0.05 mol) was stirred for 30 minutes at 100° C. The mixture was cooled, then partitioned between CH2Cl2 and water. The layers were separated. The organic phase was filtered over dicalite. The organic filtrate was dried, filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 5.2 g (35%) of 4-(2-chloroethyl)-1-(3,4-dichlorophenyl)-piperazine (interm. 9).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between CH2Cl2 and water
  3. customThe layers were separated
  4. filtrationThe organic phase was filtered over dicalite
  5. customThe organic filtrate was dried
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d79e7e555f784a32b34d2bba6eaeeb0f
Source dataset
uspto-grants-2001_05
Patent number
US06224849B1

Reaction notes

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