Pyridine → HCID 15240671, compound

HRID 1654625Notes

Reaction equation

HRID 1654625 reaction equation
N1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:26][C:27]([NH:37][CH:38]([CH3:42])[C:39](=[O:41])[CH3:40])([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1)[CH3:28]>ClCCl.O>[CH3:28][C:27]([N:37]([CH:38]([CH3:42])[C:39](=[O:41])[CH3:40])[C:23](=[O:24])[CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1)[CH3:26]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 15240678HCID 15240678, compound

Product 1

HCID 15240671HCID 15240671, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In 15 ml of dichloromethane containing 2.0 g of pyridine and 1.0 g of N-ethyl-N,N-diisopropylamine, 3.5 g of 2-phenylacetyl chloride was added dropwise to 2.5 g of N-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-N-(1-methyl-2-oxopropyl)amine at room temperature. After stirring at room temperature for 1 hour, the solution was poured into water, and then extracted with ethyl acetate. Next, the solution was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to obtain 1.7 g of N-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-N-(1-methyl-2-oxopropyl)-2-phenylacetamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washNext, the solution was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-679522ee878742e1b6b466b58707be2b
Source dataset
uspto-grants-1995_04
Patent number
US05409886

Reaction notes

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