Water → 3-{N-[2-(chroman-3-yl)ethyl]amino}propionic acid hydrochloride

HRID 1196025Notes

Reaction equation

HRID 1196025 reaction equation
[OH-].[Na+].[ClH:3].[O:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH2:5]1.O>CO>[ClH:3].[O:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14838449N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride

Product 1

HCID 678559853-{N-[2-(chroman-3-yl)ethyl]amino}propionic acid hydrochlorideYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21 ml (42 mmol) of 2N sodium hydroxide solution are added at room temperature while stirring to a solution of 2.99 g (10 mmol) of N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride in 60 ml of methanol. After 5 minutes, 40 ml of water are added to the reaction mixture which is then stirred for 30 minutes at 50°-60°. After cooling, the mixture is concentrated by evaporation in vacuo. The residue is dissolved in 30 ml of water, and then 10 ml of hydrochloric acid (36% strength) are added and the whole is cooled in an ice bath. The crystals formed are filtered off with suction. 2.5 g (87.5%) of N-[2-(chroman-3-yl)ethyl]-N-(2-carboxyethyl)-amine hydrochloride are obtained (m.p. 186°-188°).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated by evaporation in vacuo
  3. dissolutionThe residue is dissolved in 30 ml of water
  4. addition10 ml of hydrochloric acid (36% strength) are added
  5. temperaturethe whole is cooled in an ice bath
  6. customThe crystals formed
  7. filtrationare filtered off with suction

Sources & evidence

ORD record
ord-d41d3427542c4d488dc527e220dbda5e
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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