Water → 2-(4-{5-[1,1,1,3,3,3-Hexafluoro-2-(4-methoxybenzyloxy)propan-2-yl]-4-propylpyridin-2-yl}piperazin-1-yl)ethyl acetate

HRID 1038513Notes

Reaction equation

HRID 1038513 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH3:21])[C:16]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:15][N:14]=2)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[C:32](=[O:35])([O-])[O-].[K+].[K+].CO[CH:40](Cl)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH3:21])[C:16]([C:22]([O:31][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:35][CH3:32])=[CH:43][CH:42]=3)([C:23]([F:26])([F:25])[F:24])[C:27]([F:30])([F:28])[F:29])=[CH:15][N:14]=2)[CH2:11][CH2:12]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 11062637Methoxybenzyl chloride2×HCID 866471772-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetate

Product 1

HCID 866471792-(4-{5-[1,1,1,3,3,3-Hexafluoro-2-(4-methoxybenzyloxy)propan-2-yl]-4-propylpyridin-2-yl}piperazin-1-yl)ethyl acetateYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetate (211 mg, 0.461 mol) was dissolved in N,N′-dimethylformamide (2.3 mL), and added potassium carbonate (191 mg, 1.38 mmol) at room temperature. Under ice-cold conditions, methoxybenzyl chloride (125 μL, 0.923 mmol) was added, and the mixture was stirred at room temperature overnight. Subsequently, potassium carbonate (96 mg, 0.690 mmol) was further added at room temperature, methoxybenzyl chloride (63 μL, 0.462 mmol) was added under ice-cold conditions, and the mixture was stirred at room temperature for 8 hours. The reaction solution was added water, extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The title compound (479 mg) was obtained as a red-brown oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 8 hours
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e9694551891f456dadce016f706eee4b
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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