Aluminium lithium hydride → HCID 59321372, compound

HRID 1800819Notes

Reaction equation

HRID 1800819 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:8][NH2:9])([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68594997HCID 68594997, compound

Product 1

HCID 59321372HCID 59321372, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-4-(pyridin-4-yl)piperidine-4-carbonitrile (0.200 g, 0.994 mmol crude) in tetrahydrofuran (10 mL) was slowly added to a suspension of lithium aluminum hydride (0.075 g, 1.99 mmol) in tetrahydrofuran (10 mL) at 23° C. The reaction was stirred overnight and quenched with sodium sulfate decehydrate. This was stirred for 1 hour, then ethyl acetate was added and the slurry was stirred for 2 more hours. Celite was added and the resulting paste was filtered on Celite. The filtrate was concentrated to afford an oil (0.120 g, 59%) which was used as such for the next reaction.

Workup

  1. customquenched with sodium sulfate decehydrate
  2. stirringThis was stirred for 1 hour
  3. additionethyl acetate was added
  4. stirringthe slurry was stirred for 2 more hours
  5. additionCelite was added
  6. filtrationthe resulting paste was filtered on Celite
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ec5e17076f0f4a22a432e8c8802cd5e7
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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