Hydrochloric Acid → HCID 71668255, compound

HRID 1507443Notes

Reaction equation

HRID 1507443 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:26])[C:10]([CH3:25])=[C:11]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:24])[CH2:22][CH3:23])[CH2:17][CH2:16]3)[O:12]2)=[CH:7][CH:6]=1)C=C.Cl.CN(C)[C:30]1[CH:35]=CC=C[CH:31]=1>>[CH2:35]([C:14]1[C:5]([OH:4])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:24])[CH2:22][CH3:23])[CH2:17][CH2:16]1)=[C:10]([CH3:25])[C:9]2=[O:26])[CH:30]=[CH2:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 117701775HCID 117701775, compound

Product 1

HCID 71668255HCID 71668255, compoundYield 87%

Conditions

Temperature
200 °C

Procedure

A solution of 7-(allyloxy)-3-methyl-2-(1-propanoylpiperidin-4-yl)-4H-chromen-4-one (920 mg, 2.59 mmol) obtained in Example 31-3 in dimethylaniline (4 mL) was heated with stirring at 200° C. for 6 hours. A 1 N aqueous hydrochloric acid solution (100 mL) was added to the reaction solution, 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 (chloroform/methanol=100/0→95/5) to obtain 798 mg of the title compound (yield: 87%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-97cd7076aca14537a433410c641c187d
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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