Phosphorus oxychloride → HCID 178472332, compound

HRID 452530Notes

Reaction equation

HRID 452530 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](OC)[N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:22])[N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178472335HCID 178472335, compound

Product 1

HCID 178472332HCID 178472332, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of trans-4-(6-methoxy-pyridin-2-yl)-cyclohexanecarboxylic acid ethyl ester (0.55 g, 2.1 mmol) in N,N-dimethylformamide (21 ml) was added phosphorus oxychloride (0.96 ml, 10 mmol) at room temperature. Stirring for 2 h at 90° C. was followed by stirring for 24 h at 120° C. After cooling to room temperature the reaction mixture was poured onto crushed ice, stirred for 10 minutes and extracted with three 100-ml portions of ethyl acetate. The combined organic layers were washed with two 50-ml portions of water and one 50-ml portion of brine, dried over anhydrous sodium sulfate and concentrated to dryness. Purification by flash-chromatography gave the title compound (0.20 g, 36%) as light yellow oil. MS m/e: 268 ([M+H]+)

Workup

  1. stirringby stirring for 24 h at 120° C
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. additionwas poured
  4. customonto crushed ice
  5. stirringstirred for 10 minutes
  6. extractionextracted with three 100-ml portions of ethyl acetate
  7. washThe combined organic layers were washed with two 50-ml portions of water and one 50-ml portion of brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness
  10. customPurification by flash-chromatography

Sources & evidence

ORD record
ord-27b992324cf443fcb155d3d38e818958
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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