Sodium Hydroxide → 1-(N-Methyl-2-piperidinyl)methyl-3-(3-quinolinecarbonyl)-1H-indole

HRID 1161610

Reaction equation

[Al+3].[Cl-].[Cl-].[Cl-].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15](Cl)=[O:16])[CH:6]=1.[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1.[OH-].[Na+]>C(Cl)Cl>[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:15]([C:7]2[CH:6]=[N:5][C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:16])=[CH:27]1

Participants

Conditions

Temperature: 23.5 °C

Procedure

To the suspension of 200 mg (1.5 mmol) of anhydrous AlCl3 in 8 ml absolute methylene chloride was added 287.4 mg (1.5 mmol) 3-quinolinecarbonyl chloride in 5 ml methylene chloride and the reaction mixture was stirred 30 min at room 22-25° C. The (N-Methyl-2-piperidinyl)methyl-1H-indole 228.3 mg (1.0 mmol) in 5 ml of methylene chloride was added by dropwise during 1.5 h and the mixture stirred 36 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml). The combined extract dried by sodium sulfate. After removing of solvents the rest (0.365 g) was purified by chromatography (silica gel, toluene-triethylamine, 10:1).

Workup

stirringthe mixture stirred 36 h
extractionextracted by ethyl acetate (3×20 ml)
extractionThe combined extract
dry with materialdried by sodium sulfate
customAfter removing of solvents the rest (0.365 g)
customwas purified by chromatography (silica gel, toluene-triethylamine, 10:1)

Sources & evidence

ORD record: ord-6b08ba8816a84485a2ac41fdbcd3abd7
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820144B2

Linked notes

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