Triethylamine → HCID 68643979, compound

HRID 2388702Notes

Reaction equation

HRID 2388702 reaction equation
[C:1]1([CH:7]2[CH:12]=[C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:10][CH2:9][N:8]2[C:18](=[O:20])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:22](=[N:28][OH:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(N(CC)CC)C>ClCCl>[C:18]([N:8]1[CH2:9][CH2:10][C:11]2([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[O:29][N:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:12]2[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6816376Ethyl chloro(hydroximino)acetateHCID 68643976HCID 68643976, compound

Product 1

HCID 68643979HCID 68643979, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-phenyl-4-(pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone in dichloromethane (15 mL) was added a solution of ethyl 2-chloro-2-(hydroxyimino)acetate (4.709 mmol, 1.4 eq.) in dichloromethane (5 ml) at 0° C. Then triethylamine (1.4 eq.) was added dropwise at same reaction conditions and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with 10% citric acid solution and extracted with dichloromethane (3×). The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate, concentrated to dryness to give the desired product, which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with 10% citric acid solution
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7cb4966bdba4478da42e06ca95fd7622
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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