4'-Fluoroacetophenone → HCID 86585521, compound

HRID 1861746Notes

Reaction equation

HRID 1861746 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C[NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:21]([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O>[CH3:21][CH:9]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)=[O:10]

Participants

6

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 3157473Methyl(2-(piperidin-1-yl)ethyl)amine

Product 1

HCID 86585521HCID 86585521, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

4′-Fluoroacetophenone (1.5 g, 10.86 mmol), N-methyl-1-piperidineethanamine (1.54 g, 10.86 mmol) and K2CO3 (1.80 g, 13.0 mmol) in dimethylacetamide (5 mL) are heated to 100° C. with vigorous stirring for 3 days. The reaction mixture is cooled, diluted with water (50 mL), and extracted with EtOAc (3×50 mL). The organic layer is dried (magnesium sulfate) and concentrated. The product is chromatographed on silica gel eluting with 0.3% NH4OH:2.7% MeOH:97% CH2Cl2 to give 1.95 g of a brown oil.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe organic layer is dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe product is chromatographed on silica gel eluting with 0.3% NH4OH

Sources & evidence

ORD record
ord-54a502173dfb4359afade4e738acd56f
Source dataset
uspto-grants-2003_03
Patent number
US06534521B2

Reaction notes

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