Dimethylformamide → Phenethylamine

HRID 1976887Notes

Reaction equation

HRID 1976887 reaction equation
[N+](C1C=CC(O[C:11](=[O:26])[C:12]([CH3:25])=[CH:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:15]=2[NH2:24])=CC=1)([O-])=O.C[N:28]([CH3:31])C=O>>[CH2:31]([NH:28][C:11](=[O:26])[C:12]([CH3:25])=[CH:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:15]=1[NH2:24])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:14]1([CH2:13][CH2:12][NH2:28])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 702156313-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

Product 2

HCID 1001PhenethylamineHCID 702148893-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amide

Procedure

Into 30 ml of dimethylformamide, 0.72 g (2.0 mmol) of (E) 3-(2-amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester obtained above and 0.48 g (4.0 mmol) of 2-phenylethylamine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were dissolved; and the mixture was reacted at room temperature for one night. The reaction liquid was concentrated under a reduced pressure, and the resulting residue was dissolved in ethyl acetate. After the resulting solution was washed and was dried with magnesium sulfate anhydride, the solvent was eliminated under a reduced pressure, whereby a crude product was obtained. This product was refined by an aminopropyl-modified type silica gel column chromatography (n-hexane/ethyl acetate=1/1), whereby 0.68 g of the aimed compound was obtained (yield: quantitative).

Sources & evidence

ORD record
ord-d4441ec896aa4ce3bcc2b20e33448731
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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