Hydrochloric Acid → HCID 67499310, compound

HRID 661356Notes

Reaction equation

HRID 661356 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2([O:18][CH3:19])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:8]2([O:18][CH3:19])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67499544HCID 67499544, compound

Product 1

HCID 67499310HCID 67499310, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 7A (2.147 g, 7.57 mmol) in dioxane (40 mL) was added 3N hydrochloric acid (25 mL). The reaction mixture was stirred at ambient temperature for 3 hours, quenched with 3N sodium hydroxide (35 mL), followed by addition of water (200 mL), extracted twice with ethyl acetate (200 mL), washed with water (200 mL) and brine, dried with anhydrous sodium sulfate, filtered and concentrated to a yellow oil. The residue was chromatographed on silica gel, eluting with 0-to-30% ethyl acetate in hexane to provide 1.698 g (94% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.17-2.31 (m, 4H), 2.54-2.65 (m, 4H), 3.01 (s, 3H), 7.42 (dd, J=7.97, 4.58 Hz, 1H), 7.94 (dd, J=8.14, 1.36 Hz, 1H), 8.54 (dd, J=4.58, 1.53 Hz, 1H). MS (DCI) m/z 240.05 (M+H)+.

Workup

  1. customquenched with 3N sodium hydroxide (35 mL)
  2. additionfollowed by addition of water (200 mL)
  3. extractionextracted twice with ethyl acetate (200 mL)
  4. washwashed with water (200 mL) and brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil
  8. customThe residue was chromatographed on silica gel
  9. washeluting with 0-to-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a015b067296b4bb98d8eda3fa70eb0de
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

Loading…