Sodium Hydroxide → HCID 86614357, compound

HRID 2265159Notes

Reaction equation

HRID 2265159 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][CH2:9][C@@H:10]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:14][CH2:13][N:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11]1.[OH-].[Na+]>C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH2:23]([N:12]1[CH2:13][CH2:14][C@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C@@H:10]([CH2:9][NH:8][S:3](=[O:5])(=[O:4])[N:2]([CH3:7])[CH3:1])[CH2:11]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 83372Dimethylsulphamoyl chloride3×HCID 68427245HCID 68427245, compound

Product 1

HCID 86614357HCID 86614357, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent3×

Procedure

39 μL of triethylamine and 18 μL of dimethylsulfamoyl chloride were added to chloroform (1 mL) solution of 41 mg of (3S*,4S*)-3-aminomethyl-1-benzyl-4-o-tolyl-piperidine obtained in Production Example 37, and stirred at room temperature for 2.5 hours. 39 μL of triethylamine and 18 μL of dimethylsulfamoyl chloride were further added to the reaction liquid, and stirred at room temperature for 1 hour. Still further, 39 μL of triethylamine and 18 μL of dimethylsulfamoyl chloride were added to the reaction liquid, and stirred at room temperature for 1 hour. Aqueous 1 M sodium hydroxide solution was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through preparative thin-layer chromatography (chloroform/methanol=10/1) to obtain 27 mg of the entitled compound.

Workup

  1. customobtained in Production Example 37
  2. stirringstirred at room temperature for 1 hour
  3. stirringstirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated saline water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. customthe residue was separated
  9. custompurified through preparative thin-layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-c7dfd9597f464c439ada899b6fa29194
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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