Iodoethane → HCID 118076039, compound

HRID 1051738Notes

Reaction equation

HRID 1051738 reaction equation
I[CH2:2][CH3:3].[CH3:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:11]=2[O:15][CH2:16][CH2:17][CH3:18])[N:6]1[C:25](=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:2]([N:22]1[CH2:23][CH2:24][CH:19]([C:10]2[C:11]([O:15][CH2:16][CH2:17][CH3:18])=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]([C:25](=[O:27])[CH3:26])[C@@H:5]([CH3:4])[CH2:14][CH2:13]3)[CH2:20][CH2:21]1)[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118076148HCID 118076148, compound

Product 1

HCID 118076039HCID 118076039, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (5 μl, 0.06 mmol) was added to a solution of (S)-1-(2-methyl-6-(piperidin-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone (20 mg, 0.06 mmol) and potassium carbonate (38 mg, 0.27 mmol) in DMF (1.0 mL), and the reaction was stirred at room temperature overnight. The reaction was quenched via the addition of water (5 mL) and extracted with ethyl acetate (2×10 mL). The organic layer was collected and further washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 50-80% methanol in ethyl acetate) to afford (S)-1-(6-(1-ethylpiperidin-4-yl)-2-methyl-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (10 mg, 51%) as a light yellow oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.96-1.06 (m, 6H), 1.15 (t, J=7.04 Hz, 3H), 1.15-1.26 (m, 1H), 1.38-1.61 (m, 4H), 1.66-1.89 (m, 2H), 2.20 (s, 3H), 2.16-2.28 (m, 2H), 2.52 (m, 2H), 2.67-2.80 (m, 2H), 2.83-2.94 (m, 1H), 2.92-3.07 (m, 3H), 3.58-3.72 (m, 2H), 4.40-4.63 (br d, J=6.75 Hz, 1H), 7.03 (br s, 2H). MS (ESI, pos. ion) m/z 359 [M+H]+.

Workup

  1. customThe reaction was quenched via the addition of water (5 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. customThe organic layer was collected
  4. washfurther washed with water (5 mL) and brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 50-80% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-5c492876c0e544fcabc4b33215b3774a
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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