Phosphorus oxychloride → HCID 15229219, compound

HRID 274866Notes

Reaction equation

HRID 274866 reaction equation
[CH:1]1([C:7]2[CH:20]=[C:19]3[C:10]([N:11]=[C:12]4[C:17](=[C:18]3O)[CH2:16][CH2:15][CH2:14][CH2:13]4)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:18]1[C:19]2[C:10]([N:11]=[C:12]3[C:17]=1[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:20]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515153HCID 178515153, compound

Product 1

HCID 15229219HCID 15229219, compound

Procedure

7-Cyclohexyl-9-hydroxy-1,2,3,4-tetrahydroacridine (15.539 g) was refluxed for 45 minutes in 100 mL of POCl3. At the end of this time the reaction mixture was concentrated under reduced pressure and the residue was distributed between water and ether. Aqueous ammonia was added portionwise with shaking until all the organic material was dissolved in the ether layer. Evaporation and recrystallization of the residue from methanol gave 14.81 g of analytically pure product, mp 89°-91° C.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated under reduced pressure
  2. additionAqueous ammonia was added portionwise
  3. dissolutionwas dissolved in the ether layer
  4. customEvaporation and recrystallization of the residue from methanol
  5. customgave 14.81 g of analytically pure product, mp 89°-91° C.

Sources & evidence

ORD record
ord-16ee7fd784b34a9495dc27c9e0f290ee
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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