Sulfuric Acid → 1-[2-(4-Chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinone

HRID 1058627Notes

Reaction equation

HRID 1058627 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][C:20]4(OCC[O:23]4)[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:14]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH2:22]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 9933392HCID 9933392, compound

Product 1

HCID 186687451-[2-(4-Chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-piperidinoneYield 119.4%

Procedure

A mixture of 0.39 g of 1-[2-(4-chloro-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4,4-ethylenedioxypiperidine and 4 ml of concentrated sulfuric acid was stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water, adjusted to pH 11 with 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution and dried, and then the solvent was evaporated to give 0.42 g of a colorless liquid. The resulting liquid was purified by alumina column chromatography using ethyl acetate—n-heptane (1:1) as an eluting solvent to give 0.32 g of colorless crystals. Recrystallization from isopropanol gave colorless needles having the melting point of from 163 to 165° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution
  3. customdried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6e764cc1149140d38073973b980f88f0
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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