Methylamine → N-methyl-4-(1,4-benzodioxin-5-yl)butanamide

HRID 581072Notes

Reaction equation

HRID 581072 reaction equation
OC1C2N=N[NH:7][C:6]=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[O:23]1[C:28]2[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][CH2:34][CH2:35][C:36]([OH:38])=O)[C:27]=2[O:26][CH:25]=[CH:24]1.CN>CN(C=O)C.C1C=CC=CC=1.ClCCl>[CH3:6][NH:7][C:36](=[O:38])[CH2:35][CH2:34][CH2:33][C:32]1[C:27]2[O:26][CH:25]=[CH:24][O:23][C:28]=2[CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 536513674-(1,4-Benzodioxin-5-yl)butanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 54480546N-methyl-4-(1,4-benzodioxin-5-yl)butanamide

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.1 g (0.75 mmol) of hydroxybenzotriazole (HOBt) and 0.14 g (0.75 mmol) of 1-(3dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) are introduced at 0° C. into a reaction mixture comprising 0.15 g (0.68 mmol) of the acid obtained in Step F dissolved in 3 ml of anhydrous DMF. After the addition of 1.02 mmol of a 10% solution of methylamine in benzene, stirring is maintained for 24 hours and then the solvent is evaporated off in vacuo. The residue obtained is taken up in dichloromethane and then washed with water. The organic phase is dried over magnesium sulphate and then concentrated in vacuo. Chromatography over silica gel (eluant:AcOEt/PE:70/30) allows isolation of the title amide in the form of a clear oil.

Workup

  1. temperatureis maintained for 24 hours
  2. customthe solvent is evaporated off in vacuo
  3. customThe residue obtained
  4. washwashed with water
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a08bbb01be8f48e4bfb7f77956e94770
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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