Water → HCID 22037921, compound

HRID 1790481Notes

Reaction equation

HRID 1790481 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][N:13]([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)(=O)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:10]1[CH2:11][CH2:12][N:13]([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:14][CH2:15]1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22037991HCID 22037991, compound

Product 1

HCID 22037921HCID 22037921, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.14 g) was suspended in THF. Into the resultant suspension was added dropwise a solution of 1-(4-acetylpiperazin-1-yl)-6-methoxyindan (0.50 g) in THF and the reaction mixture was heated under reflux while monitoring the reaction by TLC. Then the reaction solution was ice cooled and water (0.14 ml), a 5 N aqueous solution (0.14 ml) of sodium hydroxide and further water (0.42 ml) were successively added thereto followed by stirring at room temperature for 1 hr. The resulting precipitate was filtered off and washed with THF. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (methylene chloride/methanol system) to give 1-(4-ethylpiperazin-1-yl)-6-methoxyindan (0.30 g) as an oil (yield: 63%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux
  3. customthe reaction by TLC
  4. temperaturecooled
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with THF
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-311cddd1fa984dd99906ab4142f8c75b
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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