1,2-Dichloroethane → 5-{2-[4-(1H-Indol-7-ylmethyl)piperazin-1-yl]ethoxy}-2-methylquinoline

HRID 1295592Notes

Reaction equation

HRID 1295592 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>>[NH:3]1[C:41]2[C:42](=[CH:5][CH:4]=[CH:9][C:31]=2[CH2:32][N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[C:9]=3[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]4)[CH2:16][CH2:17]2)[CH:1]=[CH:2]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 112542672-Methyl-5-(2-piperazin-1-ylethoxy)quinoline

Product 1

HCID 102161605-{2-[4-(1H-Indol-7-ylmethyl)piperazin-1-yl]ethoxy}-2-methylquinolineYield 71%

Conditions

Temperature
20 °C

Procedure

A mixture of 2-methyl-5-(2-piperazin-1-ylethoxy)quinoline (0.04 g, 0.15 mmol) and indole-7-carboxyaldehyde (0.023 g, 0.15 mmol) in 1,2-dichloroethane (2.5 mL) was treated with sodium triacetoxyborohydride (50 mg, 0.24 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 (0.042 g, 71%) 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-5c9ce96774ec4abd9f4edf09f0ec6051
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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