Aluminium lithium hydride → HCID 44467888, compound

HRID 418552Notes

Reaction equation

HRID 418552 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:22]([N:12]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[CH:9]1[CH2:10][CH2:11][N:6]([CH3:4])[CH2:7][CH2:8]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57900542HCID 57900542, compound

Product 1

HCID 44467888HCID 44467888, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[benzyl-(1H-indol-5-yl)-amino]-piperidine-1-carboxylic acid ethyl ester (100 mg, 0.265 mmol) and lithium aluminum hydride (1.0 M in THF, 1.06 mL) in THF (5.0 mL) was heated under nitrogen atmosphere to reflux. After 2.5 hours the reaction mixture was cooled and quenched by addition of Na2SO4.10H2O. The resulting mixture was filtered and the inorganic salts were washed with a mixture of MeOH and DCM. The filtrate was evaporated under reduced pressure and the crude residue was purified by flash chromatography to give 54.3 mg (64% yield) of benzyl-(1H-indol-5-yl)-(1-methyl-piperidin-4-yl)-amine, MS=320 [M+H]+.

Workup

  1. temperaturewas heated under nitrogen atmosphere
  2. temperatureto reflux
  3. temperatureAfter 2.5 hours the reaction mixture was cooled
  4. customquenched by addition of Na2SO4.10H2O
  5. filtrationThe resulting mixture was filtered
  6. washthe inorganic salts were washed with a mixture of MeOH and DCM
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-09b65be34bfd48a88524a51a02ebdf9d
Source dataset
uspto-grants-2012_01
Patent number
US08093285B2

Reaction notes

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