Dichloromethane → Piperazine, 1-(3-chloropropyl)-4-(3-(trifluoromethyl)phenyl)-

HRID 1835081Notes

Reaction equation

HRID 1835081 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][CH2:24][Cl:25].C(N(CC)CC)C>CCCCCC>[Cl:25][CH2:24][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 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 3084246TFMPP hydrochloride

Product 1

HCID 3060362Piperazine, 1-(3-chloropropyl)-4-(3-(trifluoromethyl)phenyl)-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 100 mL flask was added 1-(3-trifluoromethylphenyl)piperazine HCl (5035 mg, 18.88 mmol) and 60 mL dichloromethane. 1-Bromo-3-chloropropane (1730 ul, 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-(3-Chloropropyl)-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-81c4212be9aa4534b083c14f6fcc67ae
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

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