Ethyl Acetate → HCID 11715598, compound

HRID 1879022Notes

Reaction equation

HRID 1879022 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:14])=O)[CH2:5][CH2:4]1)[CH3:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([C:9]2[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]#[N:14])[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 57438789HCID 57438789, compound

Product 1

HCID 11715598HCID 11715598, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1-ethylpiperidin-4-yl)-2-fluorobenzamide (0.46 g, 1.83 mmol) in dry N,N-dimethylformamide (4 ml) was added freshly distilled phosphoryl trichloride (0.42 ml, 4.57 mmol) and the reaction mixture was stirred for 1 h. The solution was poured on to ice and was made basic by addition of aqueous sodium carbonate (10%, 50 ml). Ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. Purification by flash column chromatography (ethyl acetate/methanol, 1:1) gave the title compound: 0.32 g (75%). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether: M.p. 156-158° C. MS m/z (relative intensity, 70 eV) 232 (M+, 12), 218 (14), 217 (bp), 147 (10), 134 (13).

Workup

  1. additionThe solution was poured on to ice
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. dry with materialthe combined organic phases was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. customPurification by flash column chromatography (ethyl acetate/methanol, 1:1)

Sources & evidence

ORD record
ord-58415870bfac462da2385599996e6c4a
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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