Phosphorus oxychloride → HCID 21241716, compound

HRID 1761529Notes

Reaction equation

HRID 1761529 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:3]=12.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469465HCID 178469465, compound

Product 1

HCID 21241716HCID 21241716, compound

Procedure

A mixture of 4.0 g of ethyl 4-hydroxy-5,6,7,8,9,10,11,12-octahydrocyclodeca[b]pyridine-3-carboxylate and 25 ml of phosphorus oxychloride is refluxed under argon for 3 hours and then evaporated to dryness under reduced pressure. A solution of the residue in methylene chloride is treated with ice and water and basified with 10N sodium hydroxide. The layers are separated, the aqueous phase is re-extracted with methylene chloride; the combined organic extract is dried with magnesium sulfate, filtered, and the solvent is removed at reduced pressure to yield ethyl 4-chloro-5,6,7,8,9,10,11,12-octahydrocyclodeca[b]pyridine-3-carboxylate as an oil.

Workup

  1. temperatureis refluxed under argon for 3 hours
  2. customevaporated to dryness under reduced pressure
  3. additionA solution of the residue in methylene chloride is treated with ice and water and basified with 10N sodium hydroxide
  4. customThe layers are separated
  5. extractionthe aqueous phase is re-extracted with methylene chloride
  6. extractionthe combined organic extract
  7. dry with materialis dried with magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-9a5d50f933f2408798d712030f68e3ee
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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