Propargyl bromide → HCID 86758141, compound

HRID 2186339Notes

Reaction equation

HRID 2186339 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH2:20][CH2:21][CH2:22][C@@H:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]1[C:29]([OH:31])=[O:30].[CH2:32](Br)[C:33]#[CH:34].C(O[CH2:40][CH3:41])(=O)C>CN(C)C=O.O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH2:20][CH2:21][CH2:22][C@@H:23]1[CH2:28][CH2:27][N:26]([CH2:32][C:33]#[CH:34])[CH2:25][C@@H:24]1[C:29]([O:31][CH2:1][C:40]#[CH:41])=[O:30]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 70174515HCID 70174515, compound

Product 1

HCID 86758141HCID 86758141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

0.95 g of potassium carbonate was added to a solution of 0.835 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid hydrochloride in 15 cm3 of anhydrous dimethylformamide, followed by 0.36 cm3 of propargyl bromide. The mixture was stirred under a nitrogen atmosphere at a temperature in the region of 70° C. for 18 hours. 100 cm3 of ethyl acetate and 100 cm3 of distilled water were added to the reaction mixture. The organic phase was separated by settling and then washed with 5 times 40 cm3 of water and 2 times 50 cm3 of a saturated sodium chloride solution. The organic solution was dried over magnesium sulfate, filtered, and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. to maximum concentration. The oil obtained was purified by chromatography on a column of silica gel (particle size 20-45 μm; diameter 2 cm; height 40 cm), elution was carried out, under a nitrogen pressure of 50 kPa, with ethyl acetate, and 50-cm3 fractions were collected. Fractions 17 to 21 were combined and concentrated under reduced pressure (5 kPa) at a temperature of 40° C. 0.300 g of prop-2ynyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)-3-piperidinecarboxylate was obtained in the form of an oil with a yellow color.

Workup

  1. customThe organic phase was separated
  2. washwashed with 5 times 40 cm3 of water and 2 times 50 cm3 of a saturated sodium chloride solution
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. to maximum concentration
  6. customThe oil obtained
  7. customwas purified by chromatography on a column of silica gel (particle size 20-45 μm; diameter 2 cm; height 40 cm), elution
  8. customwith ethyl acetate, and 50-cm3 fractions were collected
  9. concentrationconcentrated under reduced pressure (5 kPa) at a temperature of 40° C

Sources & evidence

ORD record
ord-ea1009e46ea7452290be2d44a96ecadd
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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