Piperidine → 6-Iodo-3-methanesulfonyl-2-methyl-4-piperidin-1-yl-quinoline

HRID 13662Notes

Reaction equation

HRID 13662 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH3:13])[C:3]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:2]2[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

Product 1

HCID 119639916-Iodo-3-methanesulfonyl-2-methyl-4-piperidin-1-yl-quinolineYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline (compound of example D.2) (300 mg, 0.786 mmol), piperidine (74 mg, 0.865 mmol) and N,N-diisopropyl ethyl amine (0.148 mL, 0.865 mmol) were heated in dry N,N-dimethylformamide (3 mL) for 4 h at 100° C. N,N-Dimethylformamide was evaporated at 40° C./0.1 mbar, and the residue directly purified by chromatography on silica gel in dichloromethane. One obtained 184 mg (54%) of white crystals. MS: m/z=431 (M+H).

Workup

  1. customN,N-Dimethylformamide was evaporated at 40° C./0.1 mbar
  2. customthe residue directly purified by chromatography on silica gel in dichloromethane

Sources & evidence

ORD record
ord-e5ac2e1c00fa4990b0767c41ca6bc65a
Source dataset
uspto-grants-2010_06
Patent number
US07728142B2

Reaction notes

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