1,3-Cyclohexanedione → 3-Ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one
Reaction equation
[CH3:1][C:2](=[N:7]O)[C:3](=O)[CH2:4][CH3:5].[C:9]1(=[O:16])[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1>>[CH3:1][C:2]1[NH:7][C:11]2[CH2:12][CH2:13][CH2:14][C:9](=[O:16])[C:10]=2[C:3]=1[CH2:4][CH3:5]Participants
3
Procedure
In yet a further embodiment, the invention provides a method of manufacturing molindone through a 5-step process, wherein in the 1st step 2,3-pentanedione is reacted with hydroxylamine hydrochloride to produce 2,3-pentanedione-2-oxime (SUMO-1); in the 2nd step 2,3-pentanedione-2-oxime and 1,3-cyclohexanedione are reacted to produce 2-methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydroindole (SUMO-2); in the 3rd step 2-methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydroindole reacts with bismorpholinomethane to produce molindone (SUMO-3); in the 4th step molindone is converted into a molindone salt; and in the 5th step the molindone salt is purified/recrystallized, and, optionally, various polymorphic forms of molindone salt are prepared.
Sources & evidence
- ORD record
- ord-ab2c683d34c44e12addd4a65a33f98ec
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957206B2
Reaction notes
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