Phosphorus oxychloride → HCID 21241711, compound

HRID 1761525Notes

Reaction equation

HRID 1761525 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][CH2:21][CH2:22][C:3]=12.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][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][CH2:21][CH2:22][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469466HCID 178469466, compound

Product 1

HCID 21241711HCID 21241711, compound

Procedure

A solution of 2 g of ethyl 5,6,7,8,9,10,11,12,13,14-decahydro-4-hydroxycyclododeca[b]pyridine-3-carboxylate in 25 ml phosphorus oxychloride is refluxed for 2 hours and evaporated to dryness under reduced pressure. The residue is dissolved in methylene chloride, treated with ice and basified with saturated sodium carbonate solution. The layers are separated, the aqueous phase re-extracted with methylene chloride, and the combined organic layers dried with magnesium sulfate, filtered, and evaporated to dryness to obtain ethyl 4-chloro-5,6,7,8,9,10,11,12,13,14-decahydrocyclododeca[b]pyridine-3-carboxylate as an oil.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in methylene chloride
  3. additiontreated with ice and basified with saturated sodium carbonate solution
  4. customThe layers are separated
  5. extractionthe aqueous phase re-extracted with methylene chloride
  6. dry with materialthe combined organic layers dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-89b74c2e8cba4f8ea94b256a46f12027
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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