Piperidine → HCID 22055352, compound

HRID 1829900Notes

Reaction equation

HRID 1829900 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:3]1=[O:20].CCN(CC)CC.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:3]1=[O:20]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 22055308HCID 22055308, compound

Product 1

HCID 22055352HCID 22055352, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methyl-2-oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride (Preparation 1, 65 mg, 200 μmol) in anhydrous DMF (1.5 mL) was treated with NEt3 (31 μL, 220 μmol) and piperidine (21 μL, 210 μmol), before being stirred overnight under N2. The reaction mixture was diluted with EtOAc (70 mL), before being washed with H2O (30 mL), 1 M HCl (30 mL), H2O (30 mL), saturated aqueous NaHCO3 (30 mL), H2O (30 mL), and brine (30 mL). After drying (MgSO4), the organic phase was filtered and concentrated to give a residue that was recrystallised from EtOAc-PE to furnish the title compound (40 mg, 53%): δH (CDCl3)=1.40–1.50 (m, 2H), 1.60–1.70 (m, 4H), 3.05 (t, 4H), 3.80 (s, 3H), 7.20 (s, 1H), 7.55 (d, 1H), 8.00 (dd, 1H), 8.20 (d, 1H); m/z (ES+)=375.1 [M +H]+.

Workup

  1. washbefore being washed with H2O (30 mL), 1 M HCl (30 mL), H2O (30 mL), saturated aqueous NaHCO3 (30 mL), H2O (30 mL), and brine (30 mL)
  2. dry with materialAfter drying (MgSO4)
  3. filtrationthe organic phase was filtered
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwas recrystallised from EtOAc-PE

Sources & evidence

ORD record
ord-157c6320ae074b71b6f46755a2189808
Source dataset
uspto-grants-2006_06
Patent number
US07064207B2

Reaction notes

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