Formaldehyde → 1-(Hydroxymethyl)piperidine-2,6-dione
Reaction equation
[C:1]1(=[O:8])[NH:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2]1.[CH2:9]=[O:10]>O>[CH2:9]([N:6]1[C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]1=[O:8])[OH:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Glutarimide (27 g) and a 35% formaldehyde solution (20 ml) were added to water (40 ml), and heated at about 100° C. for 1 hour over an oil bath. The water was completely distilled away from the reaction mixture using a rotary evaporator. Thus, a crude product of N-methylolglutarimide was obtained. This product was added to 200 ml of benzene without purification, and the resulting solution was heated together with phosphorus tribromide (7.5 ml) under reflux for 1 hour. Thereto, water was added and thereby the benzene layer was separated. The crude product obtained by distilling the benzene away from the benzene layer was recrystallized from an ethyl acetate/n-hexane mixture to yield about 25 g of the desired compound. Melting Point: 165° C.
Workup
- distillationThe water was completely distilled away from the reaction mixture
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-f71a541547304a2a9adc9e9550c8622f
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04629683
Reaction notes
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