2-Fluoroethyl bromide → 1-(4-Ethylpiperazin-1-yl)-3-[4-(2-fluoroethoxy)phenyl]isoquinoline

HRID 1006884Notes

Reaction equation

HRID 1006884 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[H-].[Na+].[H][H].[F:30][CH2:31][CH2:32]Br>CN(C)C=O>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:32][CH2:31][F:30])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 1357190421-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 98861311-(4-Ethylpiperazin-1-yl)-3-[4-(2-fluoroethoxy)phenyl]isoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Ethylpiperazin-1-yl)-3-(4-hydroxyphenyl)isoquinoline (0.514 g) obtained in Example 7 was dissolved in N,N-dimethylformamide (5 ml), followed by the addition of 60% sodium hydride (0.075 g). After the evolution of hydrogen was ceased, 2-fluoroethyl bromide (230 μl) was added thereto, and then heated under reflux for 8 hr. After the reaction solution was cooled to room temperature, it was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.582 g of 1-(4-ethylpiperazin-1-yl)-3-[4-(2-fluoroethoxy)phenyl]isoquinoline as a white powder. The compound was converted into a hydrochloride in a conventional manner, to give the title compound as a yellow powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hr
  3. customit was partitioned between ethyl acetate and water
  4. washThe resulting organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-585606b0be214605b43fa55a252d4479
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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