Sodium Bicarbonate → HCID 19379690, compound

HRID 2209969Notes

Reaction equation

HRID 2209969 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[C:6](=[O:15])[CH:5]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([CH:19]2[CH2:20][CH2:21][N:16]([CH2:2][CH2:3][C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]([CH3:14])[C:6](=[O:15])[CH:5]=3)[CH2:17][CH2:18]2)=[CH:23]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 19379717HCID 19379717, compound

Product 1

HCID 19379690HCID 19379690, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-bromoethyl)-1-methyl-2(1H)-quinolinone (II-7) (500 mg, 1.88 mmol), 3-(4-piperidinyl)-1H-indole (376.5 mg, 1.88 mmol) and sodium hydrogencarbonate (236.9 mg, 2.82 mmol) in dry dimethylformamide 5 ml was allowed to react 90 ° C. for 3.5 hours. The reaction mixture was poured into ice-water and then the separated solid was filtered off by aspiration. The solid was washed with water and dried. The obtained solid was dissolved in developing solvent (chloroform: methanol=95:5) and purified by silica gel column chromatography. After removing first eluted impurity, a colorless solution was collected and the solvent was distilled off to give the desired product (III-17) (536 mg) as white crystals (yield 74.0%, mp 79°-81 ° C. (benzene-hexane)).

Workup

  1. customto react 90 ° C. for 3.5 hours
  2. filtrationthe separated solid was filtered off by aspiration
  3. washThe solid was washed with water
  4. customdried
  5. dissolutionThe obtained solid was dissolved
  6. custompurified by silica gel column chromatography
  7. customAfter removing first eluted impurity
  8. customa colorless solution was collected
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-78b2a1cffa2b40eeb3ccacdce7930e75
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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