Sodium hydride → 1-(4-Methyl-2-pyridyl)-4-[(E)-3,3,4,4,4-pentafluorobut-1-enyl]sulfonyl-piperazine

HRID 1775346Notes

Reaction equation

HRID 1775346 reaction equation
C(OP([CH2:9][S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])(OCC)=O)C.[H-].[Na+].[F:28][C:29]([F:38])([C:34]([F:37])([F:36])[F:35])[CH:30](OC)O>C1COCC1>[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([S:10](/[CH:9]=[CH:30]/[C:29]([F:38])([F:28])[C:34]([F:37])([F:36])[F:35])(=[O:11])=[O:12])[CH2:18][CH2:17]2)[CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1084041-Propanol, 2,2,3,3,3-pentafluoro-1-methoxy-HCID 898258041-(Diethoxyphosphorylmethylsulfonyl)-4-(4-methyl-2-pyridyl)piperazine

Product 1

HCID 717652901-(4-Methyl-2-pyridyl)-4-[(E)-3,3,4,4,4-pentafluorobut-1-enyl]sulfonyl-piperazineYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(diethoxyphosphorylmethylsulfonyl)-4-(4-methyl-2-pyridyl)piperazine (242 mg, 0.618 mmol) in anhydrous THF (25 ml) were added molsieves 4A and sodium hydride (60%, 38 mg, 0.95 mmol) under nitrogen and the mixture was stirred at room temperature for 10 minutes. The mixture was cooled to 0° C. and 2,2,3,3,3-pentafluoro-1-methoxy-propan-1-ol (300 mg, 1.67 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and then allowed to reach room temperature over one hour. The mixture was filtered through kieselguhr, concentrated under reduced pressure and the residue was purified by column chromatography (reveleris, gradient from 0 to 100% ethyl acetate in n-heptane) to yield 130 mg (0.337 mmol, yield 55%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at 0° C. for 30 minutes
  3. waitto reach room temperature over one hour
  4. filtrationThe mixture was filtered through kieselguhr
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (reveleris, gradient from 0 to 100% ethyl acetate in n-heptane)
  7. customto yield 130 mg (0.337 mmol, yield 55%)

Sources & evidence

ORD record
ord-2d59096a40f84be398e9ce6559225744
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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