Potassium Iodide → HCID 86592019, compound

HRID 1785883Notes

Reaction equation

HRID 1785883 reaction equation
[CH3:1][C@H:2]1[CH2:11][C@@H:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[C:19](=[O:22])([O-])[O-].[K+].[K+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1.[I-].[K+].[CH3:37]N(C)C=O>>[CH3:34][O:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C@H:10]([N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:22])[CH3:37])[CH2:11][C@@H:2]1[CH3:1]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 715776HCID 715776, compoundHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 86592019HCID 86592019, compound

Procedure

(±)-Cis-N-[1-(3-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide was synthesized by dissolving (±)-cis-(2-methyl-1,2,3,4-tetrahydroquinol-4-yl)aniline in dimethylformamide and adding potassium carbonate (1.0-10.0 equiv.), and the 1-bromomethyl-3-methoxy-benzene (1.1-3.0 equiv), catalytic potassium iodide and was stirred at room temperature for 18 hours. The reaction mixture was filtered for removal of inorganic salts and concentrated. The crude mixture was purified by flash chromatography on silica gel using gradient elution hexane-ethyl acetate (5-20%). The corresponding aniline was then acylated as previously described in general procedure A to give (±)-cis-N-[1-(3-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide.

Workup

  1. custom(±)-Cis-N-[1-(3-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide was synthesized
  2. filtrationThe reaction mixture was filtered for removal of inorganic salts
  3. concentrationconcentrated
  4. customThe crude mixture was purified by flash chromatography on silica gel using gradient elution hexane-ethyl acetate (5-20%)

Sources & evidence

ORD record
ord-d0d62d144b904d71baaab5ea2a058acc
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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