Formaldehyde → 1-Ethyl-4-(hydroxymethyl)piperazine-2,3-dione
Reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][C:5](=[O:9])[C:4]1=[O:10])[CH3:2].[CH2:11]=[O:12]>Cl>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:11][OH:12])[C:5](=[O:9])[C:4]1=[O:10])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1-ethylpiperazine-2,3-dione (2.13 g, 15 mmol) in 30% aqueous (methanol free) formaldehyde (15 mmol) potassium hydroxide (150 mg, 2.7 mmol) was added and the mixture stirred at 50° C. for 7 days. It was neutralized with 5 N aqueous hydrochloric acid (50 μl) to pH=7. The mixture was evaporated at 15 mm and then dried in high vacuo (0.0013 mbar) (0.001 mm) to give 1-ethyl-4- (hydroxymethyl)-piperazine-2,3-dione as a colourless solid (100%). NMR-spectrum in CDCl3: 1.15 (broad signal, 1H), 1.15 (t, 3H, J=7 Hz), 3.47 (q, 2H, J=7 Hz), 3.54 (m, 2H), 3.68 (m, 2H), 4.88 (s, 2H) ppm.
Workup
- customThe mixture was evaporated at 15 mm
- customdried in high vacuo (0.0013 mbar) (0.001 mm)
Sources & evidence
- ORD record
- ord-1896bacf1ee24ef1b74871aae3e5d2e0
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06482818B2
Reaction notes
Loading…