Water → HCID 11651507, compound

HRID 2263496Notes

Reaction equation

HRID 2263496 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23].O>C(#N)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH3:23])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 24904197HCID 24904197, compound

Product 1

HCID 11651507HCID 11651507, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(2,3-difluorophenyl)piperidine (0.41 g, 2.08 mmol) in acetonitrile (4 ml), was added potassium carbonate (0.57 g, 4.16 mmol) and 1-iodoethane (0.163 ml, 2.12 mmol) and the mixture was heated to 120° C. in a sealed tube under microwave radiation for 1200 s. Water (50 ml) was added and the mixture was extracted with ethylacetate (3×40 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The oily residue was purified by flash column chromatography (ethylacetate/methanol, 1:1) to give the title compound (0.31 g). MS m/z (reL. intensity, 70 eV) 225 (M+, 20), 224 (14), 211 (13), 210 (bp), 127 (8).

Workup

  1. extractionthe mixture was extracted with ethylacetate (3×40 ml)
  2. dry with materialThe combined organic phases was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe oily residue was purified by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-c9ea330beefe4a3abdd4c38e26eaa319
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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