Hydrochloric Acid → N-Benzyl-N-(2-oxoethyl)-3-phenethyloxy-propanamide

HRID 2234171Notes

Reaction equation

HRID 2234171 reaction equation
[CH2:1]([N:8]([CH2:22][CH:23](OCC)[O:24]CC)[C:9](=[O:21])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.ClCCl>O1CCOCC1>[CH2:1]([N:8]([CH2:22][CH:23]=[O:24])[C:9](=[O:21])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 68703095N-Benzyl-N-(2,2-diethoxyethyl)-3-phenethyloxy-propanamide

Product 1

HCID 86258389N-Benzyl-N-(2-oxoethyl)-3-phenethyloxy-propanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Benzyl-N-(2,2-diethoxyethyl)-3-phenethyloxy-propanamide (Example 4a), 0.3 g) was dissolved in anhydrous dioxane (7 mL) and treated with concentrated hydrochloric acid (2 mL) at ambient temperature. The resultant solution was stirred at ambient temperature for 2.5 hours. The reaction mixture was poured into dichloromethane (20 mL) and washed with water (2×20 mL) and brine (20 mL). The organic layer was isolated, dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.19 g) as a viscous oil.

Workup

  1. washwashed with water (2×20 mL) and brine (20 mL)
  2. customThe organic layer was isolated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ee342cdcfc148d4ba76ec72baf30354
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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