Potassium Carbonate → HCID 13560811, compound

HRID 1285528Notes

Reaction equation

HRID 1285528 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Cl.C(=O)([O-])[O-].[K+].[K+].[CH3:16][CH:17]([N:19]([CH:31]([CH3:33])[CH3:32])[CH2:20][CH2:21][CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:23]#[N:24])[CH3:18].[H-].[K+].N1C=CC=CC=1CCl>O.C1(C)C=CC=CC=1>[CH3:33][CH:31]([N:19]([CH:17]([CH3:18])[CH3:16])[CH2:20][CH2:21][C:22]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)[C:23]#[N:24])[CH3:32]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 23393Picolyl chlorideHCID 82127Potassium hydrideHCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Product 1

HCID 13560811HCID 13560811, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

To a solution of 26 g (159 mmole) of 2-picolyl chloride hydrochloride in 50 ml of water was added in portions 22 g (159 mmoles) of potassium carbonate. The solution was extracted into diethyl ether, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to oily 2-picolyl chloride. A mixture of 29.0 g (119 mmol) of α-[2-[bis(1-methylethyl)amino]ethyl]-phenylacetonitrile and 17.5 g (ca. 153 mmole) of potassium hydride (as a 30% dispersion in mineral oil) was heated for thirty minutes at 65°-70° in 550 ml of toluene. To this mixture was added a solution of the previously prepared 2-picolyl chloride dissolved in 400 ml of toluene. After the reaction mixture was stirred for thirty minutes at 70°, 400 ml of water was added. The toluene layer was separated and extracted with 10% hydrochloric acid. The acidic aqueous layer was separated and made basic with aqueous sodium hydroxide, then extracted with dichloromethane. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Column chromatography on silica gel afforded 18.7 g of the title compound as an oil. nmr (CDCl3): δ(ppm) 3.4 (pseudo-d, pyridyl-CH2 (non-equivalent H's)); 6.9-7.7 (m's, aromatic CH's); 8.4-8.6 (m, pyridine 6H).

Workup

  1. extractionThe solution was extracted into diethyl ether
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to oily 2-picolyl chloride
  6. customThe toluene layer was separated
  7. extractionextracted with 10% hydrochloric acid
  8. customThe acidic aqueous layer was separated
  9. extractionextracted with dichloromethane
  10. washThe organic phase was washed with brine
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7d3e25fcc664739a7e3d980928fba0f
Source dataset
uspto-grants-1986_01
Patent number
US04567270

Reaction notes

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