Diisopropylamine → 1-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanone

HRID 2304603Notes

Reaction equation

HRID 2304603 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.CC1N([C:24]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])C1>O1CCCC1.CCCCCC.O>[Cl:32][C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:24](=[O:25])[CH2:19][C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 79634-MethylpyridineHCID 592159Aziridine, 1-(o-chlorobenzoyl)-2-methyl-HCID 178418339Butyllithium

Product 1

HCID 113792481-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanoneYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a stirred solution of diisopropylamine (15.4 mL) in dry tetrahydrofuran (100 mL) cooled at −50° C., was added a solution of 1.6 M n-butyllithium in hexane (69 mL) dropwise. After addition, the resulting mixture was stirred for 10 min at the same temperature, followed by the addition of a solution of γ-picoline (20 g) in dry tetrahydrofuran (10 mL) at −30° C. After an additional 1 h stirring, a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in dry tetrahydrofuran (10 mL) was added dropwise to the resulting mixture at −10° C. After addition the mixture was stirred for another 2 h at ambient temperature. Water (100 mL) was added to the mixture and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated under reduced pressure. The residue was purified using silica-gel column chromatography (hexane-ethyl acetate, 1:1) to give the title compound (16.4 g, yield 71%).

Workup

  1. additionAfter addition
  2. stirringAfter an additional 1 h stirring
  3. additionAfter addition the mixture
  4. stirringwas stirred for another 2 h at ambient temperature
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified

Sources & evidence

ORD record
ord-ab24449b907441d0b0fd31bcb48cf24b
Source dataset
uspto-grants-2002_08
Patent number
US06436966B1

Reaction notes

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