Piperazine → 1-(2,4-Dichlorophenyl)piperazine

HRID 1416272Notes

Reaction equation

HRID 1416272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([Cl:9])[CH:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CN(C)C(=O)C>[Cl:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 123112Benzene, 2,4-dichloro-1-fluoro-

Product 1

HCID 27375271-(2,4-Dichlorophenyl)piperazineYield 76%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 1,3-dichloro-4-fluorobenzene (Aldrich; 4.21 g), piperazine (Aldrich; 11.0 g), and N,N-dimethylacetamide (Aldrich; 15 mL) is heated at 165° C. for 6.5 h. After cooling, the mixture is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated under reduced pressure to give 4.48 g of 1-(2,4-dichlorophenyl) piperazine. 1H NMR (CDCl3) δ3.00, 3.06, 6.96, 7.19, 7.36.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between dichloromethane and aq. sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3c9e89fd5a0408d9b7462c7727760d9
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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