Ammonia → Mirtazapine
Reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20]O)[CH2:4][CH2:3]1.S(=O)(=O)(O)O.N.[OH-].[Na+]>>[CH3:1][N:2]1[CH2:7][CH:6]2[N:5]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=32)[CH2:4][CH2:3]1Participants
Conditions
- Temperature
- 10 °C
Procedure
In a 50 mL three-necked flask equipped with a mechanical stirrer, a condenser and a thermometer 1.8 g of 1-(3-hydroxymethyl pyridyl-2)-4-methyl-2-phenyl-piperazine are added to ˜5 mL of concentrated sulfuric acid that was previously cooled to 10° C. The obtained solution is mixed at room temperature for 4 hours, then heated for one hour to about 50° to 600° C. After cooling, the reaction mass is added to 25 g of ice under mixing and neutralized with a concentrated ammonia solution or sodium hydroxide. The formed precipitate is separated by filtration. The mother liquor is evaporated to dryness under vacuum. Both the formed precipitate and the residue from the mother liquor are each suspended in˜20 mL of isopropanol. The combined isopropanol extracts are evaporated to dryness. An oil is obtained which contains 1.35 g of mirtazapine (yield 80%).
Workup
- customIn a 50 mL three-necked flask equipped with a mechanical stirrer, a condenser
- additionThe obtained solution is mixed at room temperature for 4 hours
- temperatureheated for one hour to about 50° to 600° C
- temperatureAfter cooling
- additionunder mixing
- customThe formed precipitate is separated by filtration
- customThe mother liquor is evaporated to dryness under vacuum
- customThe combined isopropanol extracts are evaporated to dryness
- customAn oil is obtained which
Sources & evidence
- ORD record
- ord-033fb3941b354836b716fcda54d1053b
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576764B2
Reaction notes
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