Pyridine → 4-(4-Trifluoromethoxyphenyl)piperazine-1-carbonylchloride

HRID 856141Notes

Reaction equation

HRID 856141 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[Cl:18][C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:17][C:2]([F:1])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][N:13]([C:19]([Cl:18])=[O:21])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 230811701-(4-(Trifluoromethoxy)phenyl)piperazine

Product 1

HCID 230812344-(4-Trifluoromethoxyphenyl)piperazine-1-carbonylchlorideYield 300.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-trifluoromethoxyphenyl)piperazine (1.0 g, 4.1 mmol), triphosgene (0.42 g, 1.4 mmol), and pyridine (0.66 ml, 8.2 mmol) in toluene (20 ml) was stirred at 100° C. for 4.5 hours. To which ethyl acetate was added, and the mixture was washed with water, dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 4-(4-trifluoromethoxyphenyl)piperazine-1-carbonylchloride (1.3 g, quantitative) as a brown oil.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b88fd0cd34fa434898f866adfa3ac00a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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