Oxalyl chloride → HCID 19379071, compound

HRID 2210556Notes

Reaction equation

HRID 2210556 reaction equation
[C:1]1(=[CH:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:25])[C:22]([OH:24])=O)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.N.CC#[N:35]>C1(C)C=CC=CC=1.CN(C=O)C.O>[C:1]1(=[CH:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:25])[C:22]([NH2:35])=[O:24])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 15587892HCID 15587892, compoundHCID 19379064HCID 19379064, compound

Product 1

HCID 19379071HCID 19379071, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a magnetically stirred suspension of [4-(3-cyclopentylidenemethyl-4-methoxy-phenyl)piperidin-1-yl]-oxo-acetic acid (1.2 mmol, 0.40 g) in dry toluene (15 mL) at room temperature was added oxalyl chloride (2.0M in CH2Cl2 ; 1.3 mmol, 0.65 mL) dropwise over 10 minutes, followed by DMF (3 drops) to promote gas evolution. The resulting homogeneous solution stirred at room temperature for 45 minutes, at which time saturated NH3 /CH3CN (15 mL) was added dropwise over 15 minutes. A white solid precipitated out of solution as the mixture was stirred for another 3/4 hour. At that time, TLC analysis shows reaction to be complete. The solution was diluted with H2O to dissolve the white precipitate and then the THF was removed in vacuo. The aqueous phase was diluted with saturated aqueous NaHCO3 solution (100 mL) and then extracted with EtOAc (2×200 mL). Each organic phase was washed with H2O (1×100 mL) and then the combined organics were dried (Na2SO4) and concentrated to yield a white solid. This compound was purified via column chromatography (SiO2 : 40% EtOAc/hex) to afford a pure white solid of the title compound as a pure white solid, mp 116°-117° C. (0.7 mmol, 0.231 g, 56%).

Workup

  1. additionwas added dropwise over 15 minutes
  2. customA white solid precipitated out of solution as the mixture
  3. customreaction
  4. dissolutionto dissolve the white precipitate
  5. customthe THF was removed in vacuo
  6. additionThe aqueous phase was diluted with saturated aqueous NaHCO3 solution (100 mL)
  7. extractionextracted with EtOAc (2×200 mL)
  8. washEach organic phase was washed with H2O (1×100 mL)
  9. dry with materialthe combined organics were dried (Na2SO4)
  10. concentrationconcentrated
  11. customto yield a white solid
  12. customThis compound was purified via column chromatography (SiO2 : 40% EtOAc/hex)

Sources & evidence

ORD record
ord-bd2ce777ebff44cabd529c475311aa99
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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