Oxalyl chloride → HCID 15295466, compound

HRID 2210549Notes

Reaction equation

HRID 2210549 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:25])[C:22](O)=[O:23])[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>[CH:1]1([O: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:23])[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

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 15295465HCID 15295465, compoundHCID 15587892HCID 15587892, compound

Product 1

HCID 15295466HCID 15295466, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a magnetically-stirred suspension of 2-[4-(3-cyclopentyloxy-4-methoxyphenyl) piperidin-1-yl]-2-oxo-acetic acid (2.5 mmol, 0.868 g) in dry toluene (25 mL) at room temperature was added oxalyl chloride (2.0M solution in CH2Cl2 ; 2.75 mmol, 1.38 mL) dropwise over 10 minutes, followed by DMF (4 drops). The resulting homogenous solution was stirred at room temperature for 30 minutes, after which time saturated NH3 /CH3CN (25 mL) was added dropwise over 30 minutes. A white solid precipitated out of solution, and the heterogeneous mixture was stirred for 1 hour at room temperature. The solution was diluted with H2O to dissolve the white precipitate and the volatiles were removed in vacuo. The solid was partitioned between saturated NaHCO3 (150 mL) and EtOAc (150 mL) and the aqueous phase was extracted with EtOAc (3×150 mL). The combined organic layers were washed with H2O (300 mL), dried (Na2SO4) and concentrated in vacuo to yield the title compound as a white foam, mp=66°-66.5° C. (1.8 mmol, 0.640 g, 74% yield).

Workup

  1. customA white solid precipitated out of solution
  2. stirringthe heterogeneous mixture was stirred for 1 hour at room temperature
  3. additionThe solution was diluted with H2O
  4. dissolutionto dissolve the white precipitate
  5. customthe volatiles were removed in vacuo
  6. customThe solid was partitioned between saturated NaHCO3 (150 mL) and EtOAc (150 mL)
  7. extractionthe aqueous phase was extracted with EtOAc (3×150 mL)
  8. washThe combined organic layers were washed with H2O (300 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae9e01ec0f554bf6aafd19cda00843a0
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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