Dichloromethane → 1-(2-Chloroethyl)-4-[3-(trifluoromethyl)phenyl]piperazine

HRID 1835079Notes

Reaction equation

HRID 1835079 reaction equation
Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.ClCCl.Br[CH2:22][CH2:23][Cl:24].C(N(CC)CC)C>CCCCCC>[Cl:24][CH2:23][CH2:22][N:13]1[CH2:14][CH2:15][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:2])([F:16])[F:17])[CH:5]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 78491-Bromo-2-ChloroethaneHCID 8471TriethylamineHCID 3084246TFMPP hydrochloride

Product 1

HCID 112548451-(2-Chloroethyl)-4-[3-(trifluoromethyl)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 100 mL flask was added 4-(3-trifluoromethylphenyl)piperazine HCl (5035 mg, 18.88 mmol) and 60 mL dichloromethane. 1-Bromo-2-chloroethane (1730 μl, 20.78 mmol, 1.10 eq) was added, then triethylamine (5.25 mL, 37.7 mmol, 2.00 eq). The solution was refluxed for 9 hours, then cooled to 25° C. 100 mL of hexane was then added, and the resulting suspension was vacuum filtered. The filtrate was concentrated in vacuum and purified by column chromatography using dichloromethane as eluant resulting in an oil of 1-(2-Chloroethyl)-4-(3-trifluoromethylphenyl)piperazine.

Workup

  1. temperatureThe solution was refluxed for 9 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuum
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-b9ef25334f2040aca51277d5f32cb5ea
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

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