Piperidin-4-ol → 1-(6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-yl)-piperidin-4-ol

HRID 13663Notes

Reaction equation

HRID 13663 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].[OH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]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:22]1[CH2:23][CH2:24][CH:19]([OH:18])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

Product 1

HCID 120018071-(6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-yl)-piperidin-4-olYield 62.1%

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), 4-hydroxypiperidine (87 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 0.5 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/methanol 20:1. One obtained a yellow oil which was triturated with ethyl acetate and the resulting white crystals were filtered off. One obtained 218 mg (62%) of white crystals. MS: m/z=447 (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/methanol 20:1
  3. customOne obtained a yellow oil which
  4. customwas triturated with ethyl acetate
  5. filtrationthe resulting white crystals were filtered off

Sources & evidence

ORD record
ord-8fa4444c411d45babcf101c0e2e10778
Source dataset
uspto-grants-2010_06
Patent number
US07728142B2

Reaction notes

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