(Z)-1-[2-(benzyloxy)ethyl]-4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazine → 2-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethanol

HRID 1038525Notes

Reaction equation

HRID 1038525 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:32][CH2:33][O:34][CH3:35])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2/[CH:36]=[CH:37]\[CH3:38])[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[C].[Pd]>[F:26][C:24]([F:25])([F:27])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15]2)=[C:18]([CH2:36][CH2:37][CH3:38])[CH:19]=1)([O:32][CH2:33][O:34][CH3:35])[C:28]([F:31])([F:30])[F:29]

Participants

4

Reactant 1

HCID 86647183(Z)-1-[2-(benzyloxy)ethyl]-4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazine

Product 1

HCID 866471852-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethanolYield 28.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(Z)-1-[2-(benzyloxy)ethyl]-4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazine (33 mg, 0.0604 mmol) was dissolved in methanol (4 mL), added palladium carbon (3.3 mg), and the mixture was stirred at room temperature for 12 hours under a hydrogen atmosphere. The reaction solution was filtered through a pad of celite, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (7.8 mg (yield 24%)) was obtained as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-24a3c169d23648dc8f4da48263eb96f2
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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