Pyridine → HCID 69954038, compound

HRID 2301193Notes

Reaction equation

HRID 2301193 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-26ae3f06efe544c39d56a500d84392aa
Source dataset
uspto-grants-2002_12
Patent number
US06498255B2

Reaction notes

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