2-Methoxyethylamine → HCID 22594208, compound

HRID 1761012Notes

Reaction equation

HRID 1761012 reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12]Br.C(N(CC)CC)C.[CH3:22][O:23][CH2:24][CH2:25][NH2:26]>>[CH3:11][O:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:14])[N:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:12]2

Participants

4

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoate

Product 1

HCID 22594208HCID 22594208, compoundYield 30.1%

Procedure

A mixture of 2-bromomethyl-4-methoxy-benzoic acid methyl ester (1.0 g, 3.9 mmol), triethylamine (391 mg, 3.9 mmol) and 2-methoxy-ethylamine (348 mg, 4.6 mmol) was heated under reflux for 2 h. After cooling to RT the mixture was filtered and evaporated. The residue was purified by chromatography (SiO2, Heptane:EtOAc 1:1 to EtOAc) to afford the title product (260 mg, 30%) as a light yellow solid. MS m/e=221.3 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. filtrationwas filtered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, Heptane:EtOAc 1:1 to EtOAc)

Sources & evidence

ORD record
ord-a293fdc4b6e8447f93e56e1c3a4fcaa2
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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