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Diisopropylethylamine → HCID 22318660, compound

HRID 497330
Notes
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Reaction equation

HRID 497330 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[F:32][C:33]1[CH:46]=[CH:45][C:36]2[C:37]([CH2:40][CH2:41][CH2:42][CH2:43]Cl)=[N:38][O:39][C:35]=2[CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:43][CH2:42][CH2:41][CH2:40][C:37]3[C:36]4[CH:45]=[CH:46][C:33]([F:32])=[CH:34][C:35]=4[O:39][N:38]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9991338HCID 9991338, compoundHCID 10957750Piperazine, 1-[1-(4-fluorophenyl)-2-(1-piperazinyl)ethyl]-4-methyl-

Product 1

HCID 22318660HCID 22318660, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
120 °C

Procedure

0.37 g of 1-[2-(4-Fluorophenyl)-2-(4-methylpiperazino)ethyl]piperazine obtained in Example 2 (4) was dissolved in 4.0 ml of dimethylformamide, and 0.19 g of N-ethyldiisopropylamine and 0.31 g of 4-(6-fluoro-1,2-benzisoxazol-3-yl)butyl chloride were added, followed by stirring at 120° C. for 3 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 0.22 g of 1-[2-(4-fluorophenyl)-2-(4-methylpiperazino)ethyl]-4-[4-(6-fluoro-1,2-benzisoxazol-3-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-3f39e1eff92c45d691cd705a0067d5aa
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949552B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes