Aluminium lithium hydride → HCID 68525650, compound

HRID 1932540Notes

Reaction equation

HRID 1932540 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:17]1[CH2:22][CH2:21][N:20]([C:23]([C:25]2[CH:50]=[CH:49][C:28]([O:29][C:30]3[CH:48]=[CH:47][C:33]([C:34]([NH:36][C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=4)=O)=[CH:32][N:31]=3)=[CH:27][CH:26]=2)=O)[CH2:19][CH2:18]1)[C:8]1[CH:16]=[CH:15][C:14]2[O:13][CH2:12][O:11][C:10]=2[CH:9]=1>C1COCC1>[CH2:7]([N:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:25]2[CH:50]=[CH:49][C:28]([O:29][C:30]3[N:31]=[CH:32][C:33]([CH2:34][NH:36][C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:44])[F:45])=[CH:39][CH:38]=4)=[CH:47][CH:48]=3)=[CH:27][CH:26]=2)[CH2:21][CH2:22]1)[C:8]1[CH:16]=[CH:15][C:14]2[O:13][CH2:12][O:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68525217HCID 68525217, compound

Product 1

HCID 68525650HCID 68525650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.106 g, 2.80 mmol) in THF (10 mL) was added dropwise a solution of 6-[4-(4-piperonylpiperazine-1-carbonyl)-phenoxy]-N-(4-trifluoromethylphenyl)nicotinamide (0.423 g, 0.700 mmol) in THF (10 mL) under ice cooled stirring. Once the entire amount was added dropwise, the solution temperature was slowly raised, and stirred under reflux for 2 hours. After cooling, ice water (50 mL) was added to the solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1), to thereby yield 0.125 g of the title compound.

Workup

  1. temperaturecooled
  2. additionOnce the entire amount was added dropwise
  3. temperaturethe solution temperature was slowly raised
  4. stirringstirred
  5. temperatureunder reflux for 2 hours
  6. temperatureAfter cooling
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-f73a1f45d3ec4366a8872fea993c3c0d
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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