4,4-Methylenedimorpholine → Molindone

HRID 1851642Notes

Reaction equation

HRID 1851642 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

3

Reactant 2

HCID 218394,4-MethylenedimorpholineHCID 802043-Ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one

Product 1

HCID 23897Molindone

Procedure

In a specific embodiment, the invention provides a method of manufacturing molindone through a 3-step process, 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).

Sources & evidence

ORD record
ord-866f3adff819446f94c1b2fefcba2e50
Source dataset
uspto-grants-2015_02
Patent number
US08957206B2

Reaction notes

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