1,2-Dichloroethane → HCID 59729964, compound

HRID 492640Notes

Reaction equation

HRID 492640 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-6a40959959684e6ba5ed40ba76a945cd
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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