Pyridine → HCID 69954038, compound

HRID 2268168Notes

Reaction equation

HRID 2268168 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:35]=[CH:34][C:15]2[C:16]([CH2:19]CC3CCN(CC4C=CC=CC=4)CC3)=[N:17][O:18][C:14]=2[CH:13]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:6]1[C:1]([S:7]([NH2:11])(=[O:9])=[O:8])=[CH:2][CH:3]=[CH:4][CH:5]=1.[CH3:19][C:16]1[C:15]2[CH:34]=[CH:35][CH:12]=[CH:13][C:14]=2[O:18][N:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 9945661HCID 9945661, compound

Product 1

HCID 69954038HCID 69954038, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.528 mL, 4.14 mmol) was added to a cold (0° C.) solution of 6-amino-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole(0.613 g, 4.14 mmol) and pyridine (0.670 mL, 8.28 mmol) in CH2Cl2 (30 mL). After 1.3 hours, saturated sodium bicarbonate (NaHCO3) was added and the resulting mixture was stirred overnight at room temperature. The organic layer was separated and washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatograph (5% EtOAc/CH2Cl2) gave the title compound (0.867 g, 83%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel flash chromatograph (5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ee89025ba55f442ca6d39bc5e5c5e72d
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

Loading…