Dichloromethane → Cis-N-[2-Methyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydroquinolin-4-yl]-N-phenyl-acetamide

HRID 1352503Notes

Reaction equation

HRID 1352503 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:10][CH:11]1[CH2:20][CH:19]([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1.C(N(C(C)C)C(C)C)C.ClCCl>O1CCOCC1>[CH3:10][C@H:11]1[CH2:20][C@@H:19]([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 82604Nicotinoyl chlorideHCID 2837129N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

Product 1

HCID 69425438Cis-N-[2-Methyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydroquinolin-4-yl]-N-phenyl-acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Nicotinoyl chloride (1.1 eq) was added to a solution of N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (100 mg) and N-ethyl-N,N-diisopropylamine (2.2 eq) in dioxane (1 ml). The mixture was stirred overnight at room temperature. Dichloromethane was added and the organic layer was washed by water and sodium carbonate solution and dried over sodium sulfate. The solvent was removed and the mixture was purified by chromatography on silica gel (dichloromethane and ethanol (99:1)) to afford the title compound (30 mg).

Workup

  1. washthe organic layer was washed by water and sodium carbonate solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed
  4. customthe mixture was purified by chromatography on silica gel (dichloromethane and ethanol (99:1))

Sources & evidence

ORD record
ord-0d3e24c587bd42deab3a75a86b6169e3
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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