Triethylamine → HCID 66582612, compound

HRID 1972497Notes

Reaction equation

HRID 1972497 reaction equation
Cl.Cl.[O:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C@H:10]2[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[Br:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1>C(Cl)Cl>[Br:23][C:24]1[S:28][C:27]([S:29]([N:14]2[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:9][CH:6]3[CH2:5][CH2:4][O:3][CH2:8][CH2:7]3)[CH2:15]2)(=[O:31])=[O:30])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 66582587HCID 66582587, compound2×

Product 1

HCID 66582612HCID 66582612, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The (S)-2-((tetrahydro-2H-pyran-4-yl)methyl)piperazine dihydrochloride (390 mg, 1.516 mmol, Intermediate C) was dissolved in CH2Cl2 and the solution was chilled to 0° C. To this solution was added triethylamine (634 μL, 4.55 mmol) followed by 5-bromothiophene-2-sulfonyl chloride (497 mg, 1.90 mmol, Sigma-Aldrich, St. Louis, Mo.). The mixture was allowed to slowly warm to room temperature and stirring was continued for 2 h. The mixture was concentrated and the crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2) to give (3S)-1-((5-bromo-2-thiophenyl)sulfonyl)-3-(tetrahydro-2H-pyran-4-ylmethyl)piperazine (520 mg).

Workup

  1. temperatureto slowly warm to room temperature
  2. concentrationThe mixture was concentrated
  3. customthe crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e1408425b5cc41b1b44a52d4cb321217
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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