Water → 2-(Quinoxalin-6-yl)-1-(4-(3-(trifluoromethyl)-phenyl)piperidino)ethanone

HRID 2052982Notes

Reaction equation

HRID 2052982 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([OH:14])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.Cl.[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.O>CN(C=O)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([N:27]3[CH2:28][CH2:29][CH:24]([C:20]4[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:30])[F:31])[CH:19]=4)[CH2:25][CH2:26]3)=[O:14])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 184369162-(Quinoxalin-6-yl)acetic acidHCID 222528494-(3-Trifluoromethylphenyl)piperidine, HCl

Product 1

HCID 670191982-(Quinoxalin-6-yl)-1-(4-(3-(trifluoromethyl)-phenyl)piperidino)ethanoneYield 74.6%

Reagents, catalysts & solvents 2

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateCatalystHCID 6228DimethylformamideSolvent

Procedure

0.48 g (2.55 mmol) of quinoxalin-6-ylacetic acid is mixed in 25 ml of DMF, and 1.07 ml of TEA, 0.68 g (2.55 mmol) of 4-(3-(trifluoromethyl)phenyl)piperidine hydrochloride and 1.13 mg of BOP are added thereto. The mixture is heated at ambient temperature overnight, 200 ml of water are added and extraction is carried out with ethyl acetate. The organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated under reduced pressure. A dark oil is thus obtained, which oil is purified by flash chromatography on a column of silica gel, elution being carried out with ethyl acetate. 0.76 g of the title product is obtained in the form of a yellow oil.

Workup

  1. extractionextraction
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is evaporated under reduced pressure
  5. customA dark oil is thus obtained
  6. customwhich oil is purified by flash chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-d2042c9196374f709806d9079233e2b5
Source dataset
uspto-grants-2008_02
Patent number
US07326720B2

Reaction notes

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