Triethylamine → 2-(4-(4-((2,4-Dinitrophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972679Notes

Reaction equation

HRID 1972679 reaction equation
Cl.Cl.[F:3][C:4]([F:24])([F:23])[C:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.[N+:32]([C:35]1[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:36]=1[S:44](Cl)(=[O:46])=[O:45])([O-:34])=[O:33].C([O-])(O)=O.[Na+]>C(Cl)Cl>[N+:32]([C:35]1[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:36]=1[S:44]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:13]=[CH:12][C:11]([C:5]([OH:10])([C:6]([F:9])([F:8])[F:7])[C:4]([F:3])([F:23])[F:24])=[CH:16][CH:15]=2)[CH2:18][CH2:19]1)(=[O:46])=[O:45])([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-HCID 516892Sodium BicarbonateHCID 866703461,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride

Product 1

HCID 866704322-(4-(4-((2,4-Dinitrophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanolYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL resealable vial was added 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (0.27 g, 0.67 mmol, Example 91, Step 1), DCM (6 mL), triethylamine (0.47 mL, 3.4 mmol) and finally 2,4-dinitrobenzenesulfonyl chloride (0.22 g, 0.81 mmol). The mixture was stirred at room temperature for 15 min. To the reaction mixture was added saturated aqueous NaHCO3. This was stirred for 5 min and then the solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase being collected and passed through a plug of Na2SO4. The collected solution was concentrated and purified by silica gel chromatography (0 to 70% EtOAc/hexane) afforded 2-(4-(4-((2,4-dinitrophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (0.31 g) as a white solid.

Workup

  1. stirringThis was stirred for 5 min
  2. customthe solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies) with the organic phase
  3. custombeing collected
  4. concentrationThe collected solution was concentrated
  5. custompurified by silica gel chromatography (0 to 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-f9bed4a34a8d4183af176234ee8470a2
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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