Acetic Acid → 1-Nitroso-4-piperidinol
Reaction equation
[N:1]([O-:3])=O.[Na+].[OH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[N:1]([N:9]1[CH2:10][CH2:11][CH:6]([OH:5])[CH2:7][CH2:8]1)=[O:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Add a solution of sodium nitrite (13.8 g, 200 mmol) in water (40 mL) to 4-hydroxy piperidine (10.1 g, 100 mmol) in water (20 mL). Cool the mixture to 0° C. on an ice bath. Add acetic acid (8.6 mL, 150 mmol) dropwise over 20 minutes. After the addition, continue stirring at 0° C. for 30 minutes, slowly warm up to room temperature and stir at room temp for 5 hours. Add sodium carbonate (15.9 g, 150 mmol) in portion to quench the acid. Extract the reaction with ethyl acetate (3×60 mL), combine the organic, dry over sodium sulfate, filter and concentrate to afford the desired product as yellow oil. Yield: 12.9 g, (98%).
Workup
- additionAfter the addition
- temperatureslowly warm up to room temperature
- stirringstir at room temp for 5 hours
- extractionExtract
- customthe reaction with ethyl acetate (3×60 mL)
- dry with materialdry over sodium sulfate
- filtrationfilter
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-d3e46ecfeb854e46b9815c25fcb95f7f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153807B2
Reaction notes
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