Hydrochloric Acid → HCID 67499310, compound

HRID 2197585Notes

Reaction equation

HRID 2197585 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-7e2c30ab0ae641b3acd0304bfcd51be1
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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