Water → HCID 57448042, compound

HRID 2358110Notes

Reaction equation

HRID 2358110 reaction equation
F[C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.O>C(#N)C>[N:14]1([C:2]2[C:3]([C:10]([F:13])([F:12])[F:11])=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 27747833-fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 57448042HCID 57448042, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-fluoro-2-(trifluoromethyl)benzonitrile (1.2 g, 6.3 mmol) and piperazine (0.72 g, 8.4 mmol) in acetonitrile (6 ml) was heated under microwave radiation at 150° C. for 15 minutes. The reaction mixture was poured into water (50 ml) and the aqueous phase was extracted with ethylacetate (3×50 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. Purification by flash column chromatography (ethylacetate/methanol, 1:1) gave the title compound: 1.1 g. MS m/z (rel. intensity, 70 eV) 255 (M+, 16), 214 (11), 213 (bp), 171 (8), 151 (7).

Workup

  1. extractionthe aqueous phase was extracted with ethylacetate (3×50 ml)
  2. dry with materialThe combined organic phases was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-e176acaf44544abfb34b8ac1ac5e5645
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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