Aluminium lithium hydride → HCID 22397571, compound

HRID 1070700Notes

Reaction equation

HRID 1070700 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[CH2:13][N:12]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:11][CH:10]([CH3:20])[N:9]1[CH2:21][CH2:22][CH2:23][NH-:24]>C(OCC)C.C1COCC1>[CH3:7][CH:8]1[CH2:13][N:12]([C:14]2[N:15]=[CH:16][CH:17]=[CH:18][N:19]=2)[CH2:11][CH:10]([CH3:20])[N:9]1[CH2:21][CH2:22][CH2:23][NH2:24]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86586442HCID 86586442, compound

Product 1

HCID 22397571HCID 22397571, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (1.54 mmol) of LiAlH4 were added to a solution of 0.2 g (0.77 mmol) of 3-[2,6-dimethyl-4-(2-pyrimidinyl)piperazin-1-yl]propylamide in 5 ml of diethylether and 5 ml of THF. The mixture was stirred one hour at room temperature and one additional hour at reflux, then the reaction was quenched by successive addition of 50 ul of water, 50 ul of 15% aqueous NaOH and 3×50 ul water. The mixture was diluted with diethyl ether, filtered, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silicagel (CH2Cl2, EtOH, NH4OH: 45, 5, 1) to afford 0.037 g of the title compound.

Workup

  1. temperatureone additional hour at reflux
  2. customthe reaction was quenched by successive addition of 50 ul of water, 50 ul of 15% aqueous NaOH and 3×50 ul water
  3. additionThe mixture was diluted with diethyl ether
  4. filtrationfiltered
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silicagel (CH2Cl2, EtOH, NH4OH: 45, 5, 1)

Sources & evidence

ORD record
ord-12e8568884964af2bdc64c1bf83e4cf6
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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