Sodium Bicarbonate → HCID 178422954, compound

HRID 1349959Notes

Reaction equation

HRID 1349959 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.[N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([CH:30]=O)[C:24]=2[NH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([CH2:30][N:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:8]4[CH:7]=[CH:6][CH:5]=[C:4]5[C:9]=4[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]5)[CH2:16][CH2:17]3)[C:24]=2[NH:23][CH:22]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 112542672-Methyl-5-(2-piperazin-1-ylethoxy)quinolineHCID 178519440HCID 178519440, compound

Product 1

HCID 178422954HCID 178422954, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-methyl-5-(2-piperazin-1-ylethoxy)quinoline (0.04 g, 0.15 mmol) and 3H-benzimidazole-4-carboxaldehyde (0.024 g, 0.15 mmol) in 1,2-dichloroethane (5 mL) was treated with sodium triacetoxyborohydride (47 mg, 0.22 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 (0.013 g, 22%) 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-a49a168b902343999f9c63cb36a62fe6
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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