Hydrochloric Acid → HCID 70577514, compound

HRID 1414557Notes

Reaction equation

HRID 1414557 reaction equation
[O:1]1[C:6](=[O:7])[CH2:5][C:4]2([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:3][C:2]1=O.[CH3:22][NH2:23].Cl>>[CH3:22][N:23]1[C:2](=[O:1])[CH2:3][C:4]2([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][C:6]1=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 86734382HCID 86734382, compound

Product 1

HCID 70577514HCID 70577514, compound

Procedure

This anhydride is treated with excess aqueous methylamine at room temperature. After ten minutes, the solution is acidified with dilute hydrochloric acid and the monoacid-monoamide is filtered and dried. Without further purification it is treated with excess acetic anhydride at reflux for 0.5 hours, and the reaction mixture then poured into cold aqueous sodium bicarbonate. The product, extracted with ethyl acetate, is chromatographed on silica gel and eluted with 2% ethyl acetate-petroleum ether (b.p. 60°-80° C.), giving 1'-methylxanthene-9-spiro-4'-piperidin-2',6'-dione which is recrystallised from ethyl acetate-petroleum ether (b.p. 60°-80° C.), m.p. 148°-149° C.

Workup

  1. waitAfter ten minutes
  2. filtrationthe monoacid-monoamide is filtered
  3. customdried
  4. customWithout further purification it
  5. additionis treated with excess acetic anhydride
  6. temperatureat reflux for 0.5 hours
  7. additionthe reaction mixture then poured into cold aqueous sodium bicarbonate
  8. extractionThe product, extracted with ethyl acetate
  9. customis chromatographed on silica gel
  10. washeluted with 2% ethyl acetate-petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-0bf26cd1d47f44068fd81bf29a20dc58
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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