4,4-Methylenedimorpholine → Molindone
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:13])[C:9]=2[C:10]=1[CH2:11][CH3:12].[O:14]1[CH2:19][CH2:18][N:17]([CH2:20]N2CCOCC2)[CH2:16][CH2:15]1>>[CH3:12][CH2:11][C:10]1[C:9]2[C:8]([CH:7]([CH2:20][N:17]3[CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)[CH2:6][CH2:5][C:4]=2[NH:3][C:2]=1[CH3:1])=[O:13]Participants
Procedure
For the sake of convenience and without putting any limitations thereof, the methods of manufacture of molindone have been separated into several independent steps, each independent step being disclosed herein in a multiplicity of non-limiting and independent embodiments. These independent steps comprise steps 1-3 and optional steps 4 and 5, wherein in the 1st step 2,3-pentadione 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); and 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 various polymorphic forms of the molindone salt are prepared.
Sources & evidence
- ORD record
- ord-936f42ff0dbd41c0b67bc0902740f3a0
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957206B2
Reaction notes
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