Triethylamine → HCID 66582557, compound

HRID 1972461Notes

Reaction equation

HRID 1972461 reaction equation
Cl.Cl.[F:3][C:4]([F:21])([F:20])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([OH:7])[CH3:6].[Br:22][C:23]1[S:27][C:26]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:22][C:23]1[S:27][C:26]([S:28]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[CH:10]=[CH:9][C:8]([C:5]([OH:7])([CH3:6])[C:4]([F:3])([F:20])[F:21])=[CH:13][CH:12]=3)[CH2:15][CH2:16]2)(=[O:30])=[O:29])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 66582517HCID 66582517, compound

Product 1

HCID 66582557HCID 66582557, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 250-mL round-bottomed flask was charged with 1,1,1-trifluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (2.66 g, 7.65 mmol), 5-bromothiophenesulfonyl chloride (2.00 g, 7.65 mmol, Sigma-Aldrich, St. Louis, Mo.), 25 mL of CH2Cl2, and triethylamine (3.73 mL, 26.8 mmol). After stirring at room temperature for 15 min, the mixture was diluted with CH2Cl2 (50 mL) and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (0 to 50% EtOAc in hexanes) to give 2-(4-(4-((5-bromo-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (2.10 g) as an off-white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography on silica gel (0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-88960f93fb804e748316f36a49859de8
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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