4-Aminopyridine → HCID 45116443, compound

HRID 2250834Notes

Reaction equation

HRID 2250834 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:16][CH3:17]>C1COCC1.C(Cl)Cl>[CH2:15]([S:18]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)(=[O:20])=[O:19])[CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 662791-Propanesulfonyl chloride

Product 1

HCID 45116443HCID 45116443, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

47.6 g of 4-aminopyridine (0.506 mol) and 70.0 ml of triethylamine (51.1 g, 0.506 mol) were dissolved at 50° C. in 500 ml of THF. Likewise at 50° C., 57.3 ml of n-propanesulphonyl chloride (72.2 g, 0.506 mol) were added dropwise to this solution over the course of 1 h. After 19 h of stirring at 50° C. the reaction mixture was diluted with 500 ml of methylene chloride and extracted once with 500 ml of 1 N NaOH. The aqueous phase was adjusted to a pH of 5-6 with concentrated HCl, 100 ml of ethanol were added and then the mixture was extracted 5 times with 200 ml of methylene chloride. These organic phases were dried over magnesium sulphate and then the methylene chloride was removed by distillation. The 74 g of crude product obtained were recrystallized from acetonitrile. This gave 20.8 g of clean product. The constitution of the compound was verified by NMR spectroscopy.

Workup

  1. extractionextracted once with 500 ml of 1 N NaOH
  2. additionwere added
  3. extractionthe mixture was extracted 5 times with 200 ml of methylene chloride
  4. dry with materialThese organic phases were dried over magnesium sulphate
  5. customthe methylene chloride was removed by distillation

Sources & evidence

ORD record
ord-47b1914f848c49c194cd2d0130c1a090
Source dataset
uspto-grants-2008_01
Patent number
US07317112B2

Reaction notes

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