Acetic Acid → 2-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetate

HRID 1038512Notes

Reaction equation

HRID 1038512 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([C:9]1[CH:10]=[N:11][C:12]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][OH:26])[CH2:20][CH2:19]2)=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([OH:8])[C:4]([F:7])([F:6])[F:5].N1C=CC=CC=1.[C:35](O)(=[O:37])[CH3:36].CO>ClCCl>[C:35]([O:26][CH2:25][CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:12]2[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:27])([F:1])[F:28])=[CH:10][N:11]=2)[CH2:19][CH2:20]1)(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 1049PyridineHCID 866471781,1,1,3,3,3-Hexafluoro-2-{6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-propylpyridin-3-yl}propan-2-ol

Product 1

HCID 866471772-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetateYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-{6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-propylpyridin-3-yl}propan-2-ol (208 mg, 0.501 mol) was dissolved in dichloromethane (2.5 mL), added pyridine (121 μL, 1.50 mmol) and anhydrous acetic acid (142 μL, 1.50 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 3 hours. The reaction solution was added methanol, stirred at room temperature for 0.5 hours. The reaction solution was concentrated in vacuo, extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The title compound (247 mg) was obtained as a red-brown oil.

Workup

  1. stirringstirred at room temperature for 0.5 hours
  2. concentrationThe reaction solution was concentrated in vacuo
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dab76b4c5c5d4da2b96dd1aed965a859
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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