Sodium Bicarbonate → HCID 19379686, compound

HRID 2209971Notes

Reaction equation

HRID 2209971 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH3:15])=[CH:7][C:6]1=[O:16].[NH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH2:2][CH2:3][CH2:4][N:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]([CH3:15])=[CH:7][C:6]3=[O:16])[CH2:18][CH2:19]2)=[CH:24]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 19379688HCID 19379688, compound

Product 1

HCID 19379686HCID 19379686, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-(3-chloropropyl)-4-methyl-2(1H)-quinolinone (VI-4) (455 mg, 1.93 mmol), 3-(4-piperidinyl)-1H-indole (350 mg, 1.75 mmol) and sodium hydrogencarbonate (220 mg, 2.63 mmol) in dry dimethylformamide 6 ml was allowed to react at 90 ° C. for 15 hours. Ice-water was poured into the reaction mixture and then the separated solid was filtered off by aspiration. The solid was dissolved in chloroform, then dried and the solvent was distilled off under the reduced pressure. The residue was dissolved in developing solvent (chloroform: methanol=9:1) and purified by silica gel column chromatography. After removing the first eluted impurity, a colorless solution was collected and the solvent was distilled off to give the desired product (VII-4) (450 mg) as a pale yellow solid (yield 64.4%, mp 74°-77 ° C.).

Workup

  1. customto react at 90 ° C. for 15 hours
  2. filtrationthe separated solid was filtered off by aspiration
  3. dissolutionThe solid was dissolved in chloroform
  4. customdried
  5. distillationthe solvent was distilled off under the reduced pressure
  6. dissolutionThe residue was dissolved
  7. custompurified by silica gel column chromatography
  8. customAfter removing the first eluted impurity
  9. customa colorless solution was collected
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-35cce541101b41b6aa2f175bad739c10
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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