Oxalyl chloride → (E)-4,4,4-Trifluoro-1-[4-(4-methyl-2-pyridyl)piperazin-1-yl]but-2-en-1-one

HRID 1775363Notes

Reaction equation

HRID 1775363 reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH3:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1>ClCCl.CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([N:26]1[CH2:27][CH2:28][N:23]([C:19]2[CH:18]=[C:17]([CH3:16])[CH:22]=[CH:21][N:20]=2)[CH2:24][CH2:25]1)=[O:6]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 27600581-(4-Methylpyridin-2-yl)piperazineHCID 57096144,4,4-Trifluorocrotonic acid

Product 1

HCID 71765249(E)-4,4,4-Trifluoro-1-[4-(4-methyl-2-pyridyl)piperazin-1-yl]but-2-en-1-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (28 mg, 0.2 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (20 μl, 0.2 mmol) was added and the resulting solution was stirred at room temperature for 5 minutes. This solution was added to a solution of 1-(4-methyl-2-pyridyl)piperazine (36 mg, 0.2 mmol) and TEA (42 μl, 0.3 mmol) in anhydrous DMF (0.5 ml) and the resulting mixture was stirred at room temperature for one hour. The mixture was diluted with ethyl acetate, washed with sat. sodium bicarbonate solution, brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was used directly in the next step. MS (multi-mode) m/z=300.1 [M+1]+.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for one hour
  2. washwashed with sat. sodium bicarbonate solution, brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8014297fb06241e687b4bf0675320a93
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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