Triethylamine → HCID 19085905, compound

HRID 962734Notes

Reaction equation

HRID 962734 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(N([CH2:22][CH3:23])CC)C>C(Cl)(Cl)Cl>[O:16]1[CH2:23][CH2:22][CH2:13][CH2:14][CH:15]1[O:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][S:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 3164136Pyridine-3-sulfonyl chloride

Product 1

HCID 19085905HCID 19085905, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 16 g of pyridine-3-sulfonyl chloride prepared as described by B. I. Alo, O. B. Familoni, F. Marsais and G. Queguiner, J. Heterocyclic Chem. 1992,29, 61-4 in 250 mL of chloroform was added to a solution of 8 g of 4-amino-1-butanol and 40 mL of triethylamine in 250 mL of chloroform at 0° C. The mixture was stirred overnight while warming to ambient temperature, the concentrated under reduced pressure to dryness. The residue was stirred with 500 mL of ethyl acetate, filtered and concentrated to dryness. To a solution of the crude N-(4-hydroxybutyl)pyridine-3-sulfonamide (28 g) in 200 mL of dichloromethane was added 30 mL of 3,4-dihydro-2H-pyran and 3 g of p-toluenesulfonic acid monohydrate. The reaction was stirred overnight, shaken with 100 mL of saturated sodium bicarbonate, dried over MgSO4, and concentrated to dryness. Chromatography of the residue over silica gel, eluting with ethyl acetate gave 20 g of N-(4-(2-tetrahydropyranyloxy)butyl)pyridine-3-sulfonamide as a thich amber oil.

Workup

  1. concentrationthe concentrated under reduced pressure to dryness
  2. stirringThe residue was stirred with 500 mL of ethyl acetate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. additionTo a solution of the crude N-(4-hydroxybutyl)pyridine-3-sulfonamide (28 g) in 200 mL of dichloromethane was added 30 mL of 3,4-dihydro-2H-pyran and 3 g of p-toluenesulfonic acid monohydrate
  6. stirringThe reaction was stirred overnight
  7. stirringshaken with 100 mL of saturated sodium bicarbonate
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. washChromatography of the residue over silica gel, eluting with ethyl acetate

Sources & evidence

ORD record
ord-b63fc0bc00174542b92426fd93240543
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

Loading…