Oxalyl chloride → N-(3,3-Diethoxypropyl)-N-phenethyl-3-phenethyloxy-propanamide

HRID 2234177Notes

Reaction equation

HRID 2234177 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH2:7]([O:15][CH2:16][CH2:17][C:18]([OH:20])=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([N:24]([CH:27]([CH3:29])C)[CH2:25][CH3:26])(C)C>ClCCl.CN(C)C=O>[CH2:7]([O:15][CH:16]([O:5][CH2:1][CH3:2])[CH2:29][CH2:27][N:24]([CH2:25][CH2:26][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:18](=[O:20])[CH2:17][CH2:16][O:15][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 154386723-(2-Phenylethoxy)propanoic acid

Product 1

HCID 68701548N-(3,3-Diethoxypropyl)-N-phenethyl-3-phenethyloxy-propanamideYield 115.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.078 g) was added dropwise to a solution of 3-phenethyloxypropanoic acid (0.10 g) in dichloromethane (10 mL), dimethyl formamide (1 drop) was added and stirring continued at room temperature for 1 hour. The mixture was subsequently concentrated, redissolved in dichloromethane (10 mL) and added dropwise to a solution of the crude 3,3-diethoxy-N-phenethyl-propan-1-amine, prepared as described in Example 8a) (0.33 g), and diisopropylethylamine (0.37 g) in dichloromethane (10 mL). The resulting mixture was stirred at room temperature for 1 hour, diluted (dichloromethane, 50 mL), washed with water (2×20 mL), brine (20 mL), dried over magnesium sulfate and concentrated to give a crude product (0.32 g). The latter was purified by passing through a plug of SCX resin, eluting with methanol (100 mL) to give the sub-titled compound as a clear oil (0.127 g).

Workup

  1. additionwas added
  2. concentrationThe mixture was subsequently concentrated
  3. dissolutionredissolved in dichloromethane (10 mL)
  4. additionadded dropwise to a solution of the crude 3,3-diethoxy-N-phenethyl-propan-1-amine
  5. customprepared
  6. stirringThe resulting mixture was stirred at room temperature for 1 hour
  7. washwashed with water (2×20 mL), brine (20 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give a crude product (0.32 g)
  11. customThe latter was purified
  12. washeluting with methanol (100 mL)

Sources & evidence

ORD record
ord-d8e851626ea64053a40a46eb1ac8b94c
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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