Sodium Sulfate → HCID 53302893, compound

HRID 1474424Notes

Reaction equation

HRID 1474424 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:18][CH3:19])=[C:15]([CH:17]=2)[NH2:16])(=[O:10])=[O:9])[CH:7]=1.[CH3:22][N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:18][CH3:19])=[C:15]([NH:16][CH:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[CH:17]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 67323495HCID 67323495, compound

Product 1

HCID 53302893HCID 53302893, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
27 °C

Procedure

5-(5-Bromo-2-methoxybenzenesulfonyl)-2-methoxyaniline (2 grams, 5.35 mmol) was added to 100 mL three necked round bottomed flask, followed by the addition of 1-methyl-4-piperidone (550 mg, 4.86 mmol), sodium sulfate (1.4 grams, 9.73 mmol) and acetic acid (40 mL) under nitrogen atmosphere. The reaction mass was stirred for 4 hours at room temperature (27° C.). Then sodium triacetoxy borohydride (3.08 grams, 14.60 mmol) was added to the reaction mass at 20-25° C. in 5 minutes. This reaction mixture was further stirred for another 2 hours at room temperature. The reaction mixture was then quenched into 100 mL water, basified to pH 9 with 50% aqueous sodium hydroxide solution under cooling (10° C.) and extracted the product with ethyl acetate (3×100 mL). The combined organic layer was washed with saturated brine solution (2×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to obtain oily mass. The technical product was further purified by column chromatography using ethyl acetate and methanol as eluents to obtain the title product. Yield: 1.56 grams.

Workup

  1. stirringThis reaction mixture was further stirred for another 2 hours at room temperature
  2. customThe reaction mixture was then quenched into 100 mL water
  3. temperatureunder cooling (10° C.)
  4. extractionextracted the product with ethyl acetate (3×100 mL)
  5. washThe combined organic layer was washed with saturated brine solution (2×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto obtain oily mass
  10. customThe technical product was further purified by column chromatography

Sources & evidence

ORD record
ord-18313fca643546c8abe87c72e74e47b0
Source dataset
uspto-grants-2015_04
Patent number
US09018231B2

Reaction notes

Loading…