Isopropyl iodide → HCID 22318636, compound

HRID 497332Notes

Reaction equation

HRID 497332 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:31]2[CH2:36][CH2:35][N:34]([CH:37]([CH3:39])[CH3:38])[CH2:33][CH2:32]2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][C:21]=3[OH:30])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:47]([CH3:49])[CH3:48]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:31]2[CH2:36][CH2:35][N:34]([CH:37]([CH3:39])[CH3:38])[CH2:33][CH2:32]2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][C:21]=3[O:30][CH:47]([CH3:49])[CH3:48])[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 22318631HCID 22318631, compound

Product 1

HCID 22318636HCID 22318636, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.05 g of 1-[2-(4-Fluorophenyl)-2-(4-isopropylpiperazino)ethyl]-4-[4-(2-hydroxynaphthalen-1-yl)butyl]piperazine obtained in Example 7 was dissolved in 5 ml of dimethylformamide, and 0.19 g of potassium carbonate and 0.068 ml of 2-iodopropane were added, followed by stirring at 70° C. for 6 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=1:1) to give 0.03 g of 1-[2-(4-fluorophenyl)-2-(4-isopropylpiperazino)ethyl]-4-[4-(2-isopropoxynaphthalen-1-yl)butyl]piperazine as an oil.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-edaabf4ca7fe40828206c3a36c9e1b75
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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