Water → HCID 57718562, compound

HRID 1984765Notes

Reaction equation

HRID 1984765 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[C:21]([F:24])([F:23])[F:22])[C:16]#[N:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O>O1CCCC1>[N:7]1([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[C:21]([F:22])([F:23])[F:24])[CH2:16][NH2:17])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69049848HCID 69049848, compound

Product 1

HCID 57718562HCID 57718562, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Next, to a suspension of lithium aluminum hydride (44.8 mg, 1.18 mmol) in tetrahydrofuran (5.0 mL) was added 3-piperidin-1-yl-4-(trifluoromethyl)benzonitrile (100.0 mg, 0.39 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 14 hours. To the mixture was added water and extracted with ethylacetate. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (methanol:ethylacetate=1:2) to afford [3-piperidin-1-yl-4-(trifluoromethyl)benzyl]amine (46.8 mg, 46% yield).

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography on silica gel (methanol:ethylacetate=1:2)

Sources & evidence

ORD record
ord-c04dbb1848264f259061ea2e6c709703
Source dataset
uspto-grants-2009_06
Patent number
US07544716B2

Reaction notes

Loading…