Hydrochloric Acid → HCID 86258401, compound

HRID 2234172Notes

Reaction equation

HRID 2234172 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]([CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C:7](=[O:19])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.Cl.ClCCl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[O:3]=[CH:4][CH2:5][N:6]([CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C:7](=[O:19])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 68700080HCID 68700080, compound

Product 1

HCID 86258401HCID 86258401, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-Diethoxyethyl)-3-phenethyloxy-N-(3-pyridylmethyl)propanamide (Example 5a), 0.086 g) was dissolved in anhydrous dioxane (3 mL) and treated with concentrated hydrochloric acid (0.6 mL) at ambient temperature. The resultant solution was stirred at ambient temperature for 2.5 hours. The reaction mixture was then poured into dichloromethane (10 mL) and basified with saturated sodium bicarbonate. The organic layer was isolated, washed with water (2×10 mL), washed with brine (10 mL), dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound that was used in the next step without further purification.

Workup

  1. customThe organic layer was isolated
  2. washwashed with water (2×10 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3813cb06105d4d3484d7073aa9a82170
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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