Methylamine → 2-Methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

HRID 980723Notes

Reaction equation

HRID 980723 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([C:12]([O:14]CC)=O)[CH2:10][C:9](=[O:11])[NH:8][CH2:7]1)C.[CH3:18][NH2:19]>>[CH3:18][N:19]1[C:4](=[O:3])[CH2:5][C:6]2([CH2:10][C:9](=[O:11])[NH:8][CH2:7]2)[C:12]1=[O:14]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 12691859Ethyl 3-(2-ethoxy-2-oxoethyl)-5-oxopyrrolidine-3-carboxylate

Product 1

HCID 42826302-Methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

Conditions

Temperature
220 °C

Procedure

A solution of 20.3 g (0.084 mole) 3-ethoxycarbonyl-5-oxo-3-pyrrolidineacetic acid ethyl ester [J. Org. Chem. 46, 2757 (1981)]in 40 ml of 40% aqueous methylamine was stirred at room temperature overnight, then placed in an oil bath and gradually heated to 220° C. over 30 minutes allowing volatiles to distill from the open flask. The crude product was crystallized from ethanol to afford 12.56 g of the title compound, mp 201°-204° C. Analysis calculated for C8H10N2O3 : C, 52.74; H, 5.53; N, 15.38. Found: C, 52.87; H, 5.60; N, 15.25.

Workup

  1. customplaced in an oil bath
  2. distillationto distill from the open flask
  3. customThe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-7ee64ba62ec14495a07be778c93f97f5
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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