Sodium hydride → HCID 16678729, compound

HRID 2105400Notes

Reaction equation

HRID 2105400 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[C@H:20]([CH3:25])[CH2:21][NH:22][C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl.Cl[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[C@H:20]([CH3:25])[CH2:21][N:22]([CH2:30][C:31]5[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=5)[C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 16679612(R)-8-(1-isopropylpiperidin-4-yloxy)-4-methyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 16678729HCID 16678729, compoundYield 68%

Procedure

The title compound was synthesized in analogy to example 17, from (R)-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 8), sodium hydride (2.4 equivalents) and 4-(chloromethyl)pyridine hydrochloride, to give the desired product as a light yellow foam (68%).

Sources & evidence

ORD record
ord-914ae63c0a7a4124a75f85d604520a87
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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