1,2-Dichloroethane → HCID 59729964, compound

HRID 131034Notes

Reaction equation

HRID 131034 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2].C(Cl)CCl.[CH:23]1[CH:24]=[CH:25]C2N(O)N=[N:29][C:27]=2[CH:28]=1.N1CCCCC1>C(Cl)Cl>[N:29]1([C:12]([C:11]2[CH:15]=[CH:16][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:18][CH:17]=3)=[N:9][CH:10]=2)=[O:14])[CH2:25][CH2:24][CH2:23][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 59729933HCID 59729933, compound

Product 1

HCID 59729964HCID 59729964, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 6-(4-Formyl-phenoxy)-nicotinic acid (250.0 mg, 1.03 mmol), EDC (237.0 mg, 1.23 mmol), HOBt (166.2 mg, 1.23 mmol), and Piperidine (0.10 mL, 1.03 mmol) in CH2Cl2 (6 mL). After reaction stirs at room temperature under a Nitrogen atmosphere for 24 hours, concentrate the reaction mixture using a rotovap, add Ethyl acetate and wash with 0.1N HCl, 10% NaHCO3, Brine, and dry over Na2SO4. After concentrating the reaction mixture, flash chromatograph using 2:1 Ethyl acetate:Hexanes to afford 144.1 mg (45% yield) of the title compound as a white foam: 1H NMR (500 MHz, CDCl3); 1.5-1.8 (6H, m), 3.3-3.8 (4H, m), 7.0-7.1 (1H, m), 7.3-7.4 (2H, m), 7.8-8.0 (3H, m), 8.3 (1H, m), 9.9 (1H, s); MS m/z 311 (M+1).

Workup

  1. customAfter reaction stirs at room temperature under a Nitrogen atmosphere for 24 hours
  2. concentrationconcentrate the reaction mixture
  3. additionadd Ethyl acetate
  4. washwash with 0.1N HCl, 10% NaHCO3, Brine
  5. dry with materialdry over Na2SO4
  6. concentrationAfter concentrating the reaction mixture, flash chromatograph

Sources & evidence

ORD record
ord-a9b6a164b33f4fb1b195fbc7d1c30b6b
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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