Potassium Iodide → 2,3,4,4a-Tetrahydro-3-[5-(2-Pyridinyl)Pentyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

HRID 1395456Notes

Reaction equation

HRID 1395456 reaction equation
Cl.[CH2:2]1[N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[CH:6]2[CH2:5][NH:4][CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.C(N(CC)CC)C>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:4]1[CH2:3][CH2:2][N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[CH:6]2[CH2:5]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18377410HCID 18377410, compoundHCID 20339427HCID 20339427, compound

Product 1

HCID 203394162,3,4,4a-Tetrahydro-3-[5-(2-Pyridinyl)Pentyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6.2 g. (0.03 mole) of 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, hydrochloride, 7.5 g. (0.04 mole) of 5-(2-pyridyl)pentyl bromide hydrochloride, 15 g. potassium carbonate, 5 g. potassium iodide, and 0.5 ml. of triethylamine in acetone (200 ml.) is heated under reflux for 72 hours. The reaction is worked up in the usual manner, yielding the title compound as base. This is converted to dihydrochloride salt by treating an acetone solution of base with dry hydrogen chloride, m.p. 266°-69° C. (dec.).

Workup

  1. temperatureunder reflux for 72 hours

Sources & evidence

ORD record
ord-f805c071e16445bf8ac06bd490f2e1e2
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

Loading…