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

HRID 1295591
Notes
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Reaction equation

HRID 1295591 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 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

  1. customthe organic layer separated
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes