(+-)-Anabasine → HCID 659759, compound

HRID 421553Notes

Reaction equation

HRID 421553 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>N1C=CC=CC=1>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][N:15]2[S:11]([C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:13])=[O:12])[CH:22]=1

Participants

4

Reactant 2

HCID 2181(+-)-AnabasineHCID 8481N-Acetylsulfanilyl chloride

Product 1

HCID 659759HCID 659759, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 842 mg portion of 4-(acetylamino)benzene sulfonyl chloride was added under ice-cooling to a pyridine solution (10 ml) of 3-(piperidin-2-yl)pyridine and stirred at room temperature for 2 hours. The solvent was concentrated under a reduced pressure, and the thus obtained residue was mixed with ethyl acetate and then washed with water, 1 M hydrochloric acid and saturated brine. This was dried with anhydrous sodium sulfate and then concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography using chloroform:methanol (98:2) as the elution solvent, thereby obtaining 1.00 g of N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)acetamide as a yellow foamy substance. FAB-MS (Pos): 360 [M+H]+.

Workup

  1. concentrationThe solvent was concentrated under a reduced pressure
  2. additionthe thus obtained residue was mixed with ethyl acetate
  3. washwashed with water, 1 M hydrochloric acid and saturated brine
  4. dry with materialThis was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customthe thus obtained residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-904f5c4003ce488d90e1ef8479457482
Source dataset
uspto-grants-2012_01
Patent number
US08101580B2

Reaction notes

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