1,2-Dichloroethane → HCID 59729964, compound

HRID 228487Notes

Reaction equation

HRID 228487 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-dd88c641d1364a5991490d23aeb4344a
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

Loading…