Ethyl Acetate → HCID 57831197, compound

HRID 1642019Notes

Reaction equation

HRID 1642019 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.Cl[CH2:11][C:12]1[CH:24]=[CH:23][C:15]([O:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1.CC(N(C(C)C)CC)C.C(OCC)(=O)C>CS(C)=O.O>[N:18]1[CH:19]=[CH:20][CH:21]=[N:22][C:17]=1[O:16][C:15]1[CH:23]=[CH:24][C:12]([CH2:11][N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2723901PiperonylamineHCID 57831213HCID 57831213, compound

Product 1

HCID 57831197HCID 57831197, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1.47 grams (0.0096 mole) of 4-piperidone monohydrate hydrochloride, 2.1 grams (0.0096 mole) of 2-[4-(chloromethyl)phenoxy]pyrimidine, and 4.34 grams (0.0336 mole) of bis(methylethyl)ethylamine in 35 mL of dimethylsulfoxide (DMSO) was stirred at ambient temperature for about 24 hours. The reaction mixture was then diluted with 200 mL of water and was extracted two times with 200 mL of ethyl acetate. The extracts were then combined and washed two times with 75 mL of an aqueous mixture of 10% lithium chloride. The resultant organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica get using 1:2 ethyl acetate:petroleum ether as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.71 grams of the subject compound.

Workup

  1. extractionwas extracted two times with 200 mL of ethyl acetate
  2. washwashed two times with 75 mL of an aqueous mixture of 10% lithium chloride
  3. dry with materialThe resultant organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue was purified with column chromatography on silica
  7. customget
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6103a40e6904201862aa0e364e286d2
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

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