Hydrochloric Acid → N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

HRID 2234180Notes

Reaction equation

HRID 2234180 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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>O1CCOCC1>[O:3]=[CH:4][CH2:5][N:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 68703159N-(2,2-Diethoxyethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

Product 1

HCID 86625180N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-Diethoxyethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide (Example 9b), 0.18 g) was dissolved in anhydrous dioxane (5 mL) and treated with concentrated hydrochloric acid (5 mL) at room temperature. The resultant solution was stirred for 1 hour and then poured into dichloromethane (10 mL), washed with water (2×10 mL) and brine (10 mL). The organic layer was isolated, dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.12 g) as a viscous oil.

Workup

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

Sources & evidence

ORD record
ord-d66b70e361f0443e9f85c06dc12d33f5
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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