1,2-Dichloroethane → n-Propyl-4-(1,4-benzodioxin-5-yl)butanamide

HRID 581073Notes

Reaction equation

HRID 581073 reaction equation
Cl.[CH2:2]([NH2:5])[CH2:3][CH3:4].[O:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[C:10]=2[O:9][CH:8]=[CH:7]1.C(Cl)CCl>CN(C)C=O>[CH2:2]([NH:5][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]1[C:10]2[O:9][CH:8]=[CH:7][O:6][C:11]=2[CH:12]=[CH:13][CH:14]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11165Propylamine hydrochlorideHCID 536513674-(1,4-Benzodioxin-5-yl)butanoic acid

Product 1

HCID 54244989n-Propyl-4-(1,4-benzodioxin-5-yl)butanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 0.29 g (2.6 mmol) of n-propylamine hydrochloride in 7 ml of anhydrous N,N-dimethylformamide is cooled to 0° C. and then 0.33 g (3.54 mmol) of N,N-dimethylaminopyridine are added to the mixture. After the addition of 0.41 g (2.36 mmol) of the acid obtained in Step F of Example 40, 0.5 g (2.6 mmol) of EDC is added to the mixture. The solution is stirred for 12 hours under argon at room temperature and then the solvent is evaporated off in vacuo. The residue is taken up in a water/ethyl acetate (1/1) mixture and then the aqueous phase is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated under reduced pressure. Chromatography over silica gel (eluant:AcOEt/PE:70/30) yields the title amide in the form of a clear syrup.

Workup

  1. additionis added to the mixture
  2. customthe solvent is evaporated off in vacuo
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-586d13787a5f4e21aba52e6f0a46f8a1
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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