Acetic Acid → HCID 117701619, compound

HRID 1507446Notes

Reaction equation

HRID 1507446 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([CH3:22])=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][CH2:13]3)[O:9]2)=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.[C:34](O)(=[O:36])C>>[OH:1][C:2]1[C:11]([CH:34]=[O:36])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([CH3:22])=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][CH2:13]3)[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 117701717HCID 117701717, compound

Product 1

HCID 117701619HCID 117701619, compoundYield 50%

Conditions

Temperature
100 °C

Procedure

A solution of 7-hydroxy-3-methyl-2-(1-propanoylpiperidin-4-yl)-4H-chromen-4-one (1.07 g, 3.39 mmol) obtained in Example 31-2 and hexamethylenetetramine (3.33 g, 23.75 mmol) in acetic acid (20 mL) was heated with stirring at 100° C. for 3 hours. The reaction solution was concentrated under reduced pressure. Water (16 mL) and concentrated hydrochloric acid (8 mL) were added to the obtained residue, and the mixture was heated with stirring at a bath temperature of 80° C. for 1 hour. The reaction solution was allowed to cool, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=40/60→0/100) to obtain 584 mg of the title compound (yield: 50%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater (16 mL) and concentrated hydrochloric acid (8 mL) were added to the obtained residue
  3. temperaturethe mixture was heated
  4. stirringwith stirring at a bath temperature of 80° C. for 1 hour
  5. temperatureto cool
  6. additionwater was added
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationThe desiccant was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=40/60→0/100)

Sources & evidence

ORD record
ord-4db48217d14247cabf642dca4ea01e65
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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