Methyl Acrylate → HCID 15114470, compound

HRID 1032415Notes

Reaction equation

HRID 1032415 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][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:11]1>CO>[O:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18][CH2:19][CH:10]1[CH2:9][CH2:8][NH:7][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 15027460HCID 15027460, compound

Product 1

HCID 15114470HCID 15114470, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.01 g (35 mmol) of acrylic acid methyl ester are added at 0°-5°, while stirring, to a solution of 6.2 g (35 mmol) of 2-(2-aminoethyl)chroman in 200 ml of methanol. Stirring is continued for a further 16 hours at 0°-5° and the mixture is then concentrated by evaporation in vacuo. 8.76 g (95.2%) of crude product are obtained and are chromatographed on 250 g of silica gel (0.040-0.063 mm) using ethyl acetate as the eluant. 5.10 g (55.4%) of N-[2-(chroman-2-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine are thus obtained in the form of a yellow oil. The N-[2-(chroman-2-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride produced therefrom using hydrochloric acid in diethyl ether crystallises from methanol/diethyl ether and melts at 152°-153°.

Workup

  1. concentrationthe mixture is then concentrated by evaporation in vacuo
  2. custom8.76 g (95.2%) of crude product are obtained
  3. customare chromatographed on 250 g of silica gel (0.040-0.063 mm)

Sources & evidence

ORD record
ord-e77cbc4511534819a6c2a8a7850b0e5e
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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