Potassium Iodide → (R)-4-Methyl-8-(3-piperidin-1-yl-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 506653Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]3[C@H:15]([CH3:20])[CH2:16][NH:17][C:18](=[O:19])[C:10]3=[CH:9][C:8]=2[CH:7]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH3:20][C@H:15]1[N:11]2[C:12]3[CH:13]=[CH:14][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:7][C:8]=3[CH:9]=[C:10]2[C:18](=[O:19])[NH:17][CH2:16]1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 8082Piperidine

HCID 11430Potassium Carbonate

HCID 68465710(R)-8-(3-chloro-propoxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Product 1

HCID 16679613(R)-4-Methyl-8-(3-piperidin-1-yl-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-oneYield 71%

Procedure

The title compound was synthesized in analogy to example 2, from (R)-8-(3-chloro-propoxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one, piperidine (commercially available), potassium carbonate and potassium iodide, to give the desired product as a light yellow solid (71%).

Sources & evidence

ORD record: ord-67e37e7ef82a4b0b8b74afe0114fa50d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786109B2

Reaction notes

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