Water → Tert-butyl 4-{6-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazine-1-carboxylate

HRID 1038551Notes

Reaction equation

HRID 1038551 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[C:11]([CH2:28][CH2:29][CH3:30])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C)C=O>[CH2:35]([O:8][C:3]([C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]2)=[C:11]([CH2:28][CH2:29][CH3:30])[CH:10]=1)([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:31])[F:32])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86647197tert-Butyl 4-[6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-3-yl]piperazine-1-carboxylate

Product 1

HCID 86647196Tert-butyl 4-{6-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazine-1-carboxylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-[6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-3-yl]piperazine-1-carboxylate (60 mg, 0.126 mmol) was dried with a vacuum pump, and dissolved in N,N-dimethylformamide (2.5 mL). Sodium hydride (7.3 mg, 0.152 mmol) and benzyl bromide (17 μL, 0.139 mmol) were added sequentially under ice-cold conditions, and the mixture was stirred at room temperature overnight. The reaction solution was added water under ice-cold conditions, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone), and the title compound (54 mg (yield 76%)) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-aed7cf0e5e76402f8466eabd8f93083d
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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