Ethyl 3-(methylamino)propanoate → HCID 21448613, compound

HRID 596870Notes

Reaction equation

HRID 596870 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][NH:7][CH3:8])[CH3:2].Cl[C:11]([C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:12]>N1C=CC=CC=1>[O:12]=[C:11]([N:7]([CH3:8])[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:9])[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 541480Ethyl 3-(methylamino)propanoateHCID 10559245Ethyl 3-chloro-2,2-dimethyl-3-oxopropanoate

Product 1

HCID 21448613HCID 21448613, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 61 g of N-methyl-β-alanine ethyl ester in 600 ml of dry pyridine there is added 82 g of ethyl 2-chloroformyl-2-methylpropionate. During the addition, which takes 30 minutes, the mixture is mechanically stirred and cooled with ice. Stirring is continued at 10° C for 30 minutes and then at 30° - 40° C for 1 hour. Next the pyridine is evaporated in vacuo, leaving a residue to which a small quantity of water is added, whereafter the mixture is extracted with ether. The extract is dried over magnesium sulphate and evaporated leaving the above-mentioned product as a liquid which is purified by distillation at reduced pressure. Yield 97 g (75%). Boiling point 134° - 136° C (1 mm). nD22 1.4565.

Workup

  1. additionDuring the addition, which
  2. temperaturecooled with ice
  3. stirringStirring
  4. waitis continued at 10° C for 30 minutes
  5. waitat 30° - 40° C for 1 hour
  6. customNext the pyridine is evaporated in vacuo
  7. customleaving a residue to which a small quantity of water
  8. additionis added, whereafter the mixture
  9. extractionis extracted with ether
  10. dry with materialThe extract is dried over magnesium sulphate
  11. customevaporated

Sources & evidence

ORD record
ord-148b5c0942b0443ca46c1bfff9749119
Source dataset
uspto-grants-1977_03
Patent number
US04012392

Reaction notes

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