Hydrochloric Acid → HCID 18538785, compound

HRID 1394340Notes

Reaction equation

HRID 1394340 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13].Cl>C1COCC1>[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH:4][CH2:1][CH2:2][CH3:3])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 8471TriethylamineHCID 226766334-[(1-Acetylpiperidin-4-yl)methyl]benzene-1-sulfonyl chloride

Product 1

HCID 18538785HCID 18538785, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Propylamine (0.586 ml, 7.13 mmol) and triethylamine (0.993 ml, 7.13 mmol) were added to a solution of 4-(1-acetylpiperidin-4-ylmethyl)benzenesulfonylchloride (1.5 g, 4.75 mmol) in THF (20 ml) and this mixture was refluxed for 5 h. After having been cooled, 1N hydrochloric acid (20 ml) was added. The resulting mixture was extracted with ethyl acetate (20 ml×2). The combined organic layers were washed with saturated sodium chloride solution (40 ml), and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel 25 g, ethyl acetate to ethyl acetate/methanol=10/1) to give the title compound (1.15 g, 71%) as pale yellow oil.

Workup

  1. temperaturethis mixture was refluxed for 5 h
  2. temperatureAfter having been cooled
  3. extractionThe resulting mixture was extracted with ethyl acetate (20 ml×2)
  4. washThe combined organic layers were washed with saturated sodium chloride solution (40 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash column chromatography (silica gel 25 g, ethyl acetate to ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-8de1091e1713461a831dd15ea9d4517b
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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