Methyl Acrylate → N-[2-(2,2-dimethyl-6-fluoro-chroman-3-yl)-ethyl]-N-(2-methoxycarbonylethyl)-amine

HRID 1196051Notes

Reaction equation

HRID 1196051 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH:4]=[CH2:5].[NH2:7][CH2:8][CH2:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:20])[CH:17]=2)[O:12][C:11]1([CH3:22])[CH3:21]>CO>[CH3:21][C:11]1([CH3:22])[CH:10]([CH2:9][CH2:8][NH:7][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:20])[CH:17]=2)[O:12]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 538627943-(2-Aminoethyl)-2,2-dimethyl-6-fluoro-chroman

Product 1

HCID 53961012N-[2-(2,2-dimethyl-6-fluoro-chroman-3-yl)-ethyl]-N-(2-methoxycarbonylethyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

While stirring at a temperature of from 0° to 5°, a solution of 0.86 g (9.9 mmol) of acrylic acid methyl ester in 10 ml of methanol is added dropwise within a period of 15 minutes to a solution of 2.23 g (10 mmol) of 3-(2-aminoethyl)-2,2-dimethyl-6-fluoro-chroman in 50 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 200 g of silica gel (0.040-0.063 mm) with ethyl acetate as eluant, yielding 1.9 g (61.4% of the theoretical yield) of N-[2-(2,2-dimethyl-6-fluoro-chroman-3-yl)-ethyl]-N-(2-methoxycarbonylethyl)-amine in the form of a light-yellow oil. The N-[2-(2,2-dimethyl-6-fluoro-chroman-3-yl)-ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride, prepared therefrom with hydrochloric acid in diethyl ether, crystallises from acetone/diethyl ether and melts at 129°-131°.

Workup

  1. stirringThe reaction mixture is then stirred for 16 hours at from 0° to 5°
  2. concentrationconcentrated by evaporation in vacuo
  3. customThe oily residue is chromatographed on 200 g of silica gel (0.040-0.063 mm) with ethyl acetate as eluant
  4. customyielding 1.9 g (61.4% of the

Sources & evidence

ORD record
ord-19631f41d6e24d21bf3023eb6a3a00a3
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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