p-Fluorophenethylamine → HCID 17375928, compound

HRID 1351289Notes

Reaction equation

HRID 1351289 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24][NH2:25])=[CH:21][CH:20]=1>O1CCCC1>[F:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24][NH:25][S:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:9])=[O:8])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 4653p-FluorophenethylamineHCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 17375928HCID 17375928, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromothiophene-2-sulfonyl chloride (600 mg) in tetrahydrofuran (5 mL) was added dropwise triethylamine (0.64 mL) and 4-fluorophenethylamine (0.36 mL) on an ice bath. After stirring for 15 minutes on an ice bath, the solution was further stirred at room temperature for 2 hours. After dilution with ethyl acetate and washing with 5N hydrochloric acid, water, an aqueous solution of saturated sodium bicarbonate and saturated sodium chloride water, the solution was dried with anhydrous sodium sulfate. Silica gel filtration was carried out, and the solvent was removed by evaporation to provide the title compound (860 mg) as a colorless oily matter.

Workup

  1. stirringthe solution was further stirred at room temperature for 2 hours
  2. washAfter dilution with ethyl acetate and washing with 5N hydrochloric acid, water
  3. dry with materialan aqueous solution of saturated sodium bicarbonate and saturated sodium chloride water, the solution was dried with anhydrous sodium sulfate
  4. filtrationSilica gel filtration
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-22706c0715454dd5b6fd340079140e23
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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