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

HRID 2372061Notes

Reaction equation

HRID 2372061 reaction equation
C([O:3][C:4]([C:6]1([CH2:12][C:13]([O:15]CC)=O)[CH2:10][C:9](=[O:11])[NH:8][CH2:7]1)=O)C.[CH3:18][NH2:19]>>[CH3:18][N:19]1[C:13](=[O:15])[CH2:12][C:6]2([CH2:10][C:9](=[O:11])[NH:8][CH2:7]2)[C:4]1=[O:3]

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 12.6 g of 2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione, mp 201-204° C.

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-6ba53aa765d24a9d9c301101944c2363
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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