HCID 21523734, compound → 4-methyl-2-homopiperazinone

HRID 917823Notes

Reaction equation

HRID 917823 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH3:11])[CH2:7][CH2:8][C:9]#[N:10])C.[H][H]>C(O)C.[Co]>[CH3:11][N:6]1[CH2:7][CH2:8][CH2:9][NH:10][C:4](=[O:3])[CH2:5]1

Participants

5

Reactant 2

HCID 21523734HCID 21523734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122365174-methyl-2-homopiperazinoneYield 75.1%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

A solution of 750 g of N-methyl-N-(2-cyanoethyl)glycine ethyl ester (prepared from methylaminopropionitrile and ethyl chloroacetate) in 1 liter of ethanol is hydrogenated in the presence of 60 g of Raney cobalt in an autoclave at a temperature of from 80° to 90°C and under a pressure of 100 to 120 atms. of hydrogen. The calculated quantity of hydrogen has been absorbed after about 1 hour. The hydrogenated solution is filtered off from the catalyst. The solid residue left after the ethanol has been evaporated is freed from any greases adhering to it by means of a little ethyl acetate, and the white product, which does not show any tendency towards discoloration in air, is fractionated in a high vacuum with 5 g of sodium methoxide. 424 g of 1-N-methyl-hexahydro-1,4-diazepin-3-one melting at 91°C are obtained.

Workup

  1. customThe calculated quantity of hydrogen has been absorbed after about 1 hour
  2. filtrationThe hydrogenated solution is filtered off from the catalyst
  3. waitThe solid residue left after the ethanol
  4. customhas been evaporated

Sources & evidence

ORD record
ord-f4508f86e54d40469a0834d7d1ca7d30
Source dataset
uspto-grants-1976_07
Patent number
US03968104

Reaction notes

Loading…