Methyl Acrylate → N-[(6-fluorochroman-3-yl)methyl]-N-(2-methoxycarbonylethyl)-amine
Reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH:4]=[CH2:5].[NH2:7][CH2:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:19])[CH:16]=2)[O:11][CH2:10]1>CO>[F:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH:9]([CH2:8][NH:7][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])[CH2:18]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
While stirring at a temperature of from 0° to 5°, a solution of 1.42 g (16.4 mmol) of acrylic acid methyl ester in 10 ml of methanol is added dropwise within a period of 15 minutes to a solution of 3.0 g (16.5 mmol) of 3-aminomethyl-6-fluoro-chroman in 80 ml of methanol. The reaction mixture is then stirred for 16 hours at from 0° to 5° and then concentrated by evaporation in vacuo. The oily residue is chromatographed on 250 g of silica gel (0.040-0.063 mm) with ethyl acetate as eluant, yielding 2.85 g of N-[(6-fluorochroman-3-yl)methyl]-N-(2-methoxycarbonylethyl)-amine in the form of a light-yellow oil. The N-[(6-fluorochroman-3-yl)methyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride, prepared therefrom with hydrochloric acid in diethyl ether, crystallizes from acetone/diethyl ether and melts at 163°-165°. The N-[(6-fluorochroman-3-yl)methyl]-N-(2-methoxycarbonylethyl)-amine cyclamate, prepared from the crude base with N-cyclohexyl-sulfamic acid, crystallizes from acetone and melts at 155°-156°.
Workup
- stirringThe reaction mixture is then stirred for 16 hours at from 0° to 5°
- concentrationconcentrated by evaporation in vacuo
- customThe oily residue is chromatographed on 250 g of silica gel (0.040-0.063 mm) with ethyl acetate as eluant
Sources & evidence
- ORD record
- ord-9986ea0ff5344c6baef62ffe4a90efde
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112855
Reaction notes
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