1,2-Dichloroethane → 6-{4-[2-(2-Methylquinolin-5-yloxy)ethyl]piperazin-1-ylmethyl}quinoxaline

HRID 1295591Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:3]=1.C(O[BH-](O[C:31](=O)[CH3:32])OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].Cl[CH2:41][CH2:42]Cl>>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH2:11][C:2]3[CH:1]=[C:42]4[C:41](=[CH:31][CH:32]=3)[N:18]=[CH:17][CH:16]=[N:15]4)[CH2:17][CH2:16]2)[N:3]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 516892Sodium Bicarbonate

HCID 5049666Sodium triacetoxyborohydride

HCID 112542672-Methyl-5-(2-piperazin-1-ylethoxy)quinoline

Product 1

HCID 101269486-{4-[2-(2-Methylquinolin-5-yloxy)ethyl]piperazin-1-ylmethyl}quinoxalineYield 61%

Conditions

Temperature: 20 °C

Procedure

A mixture of 2-methyl-5-(2-piperazin-1-ylethoxy)quinoline (0.054 g, 0.2 mmol) and quinoxaline-6-carboxyaldehyde (0.032 g, 0.2 mmol) in 1,2-dichloroethane (5 mL) was treated with sodium triacetoxyborohydride (64 mg, 0.2 mmol) and stirred at 20° C. under an atmosphere of argon for 24 h. The mixture was then treated with saturated aqueous NaHCO3 (20 mL) and the organic layer separated and purified directly by chromatography on silica (ethyl acetate to 10% methanol/ethyl acetate), to afford the title compound (0.05 g, 61%) as a solid.

Workup

customthe organic layer separated
custompurified directly by chromatography on silica (ethyl acetate to 10% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-4ca5ebafc7c24b74bda2e13e07e022b1
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244726B2

Reaction notes

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