Aluminium lithium hydride → HCID 19908330, compound

HRID 1534804Notes

Reaction equation

HRID 1534804 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:5]([CH3:16])[NH:4][C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.[OH-].[Na+].O>[CH3:16][CH:5]1[CH:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:7][CH:2]([CH3:1])[CH2:3][NH:4]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53807414HCID 53807414, compound

Product 1

HCID 19908330HCID 19908330, compoundYield 65.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5.8 g (25 mmol) of 3,6-dimethyl-5-(4-methoxyphenyl)-3,4,5,6-tetrahydro-2-pyridone in 60 ml of dry tetrahydrofuran was added dropwise under nitrogen to a suspension of 1.63 g of lithium aluminium hydride (63 mmol) in 25 ml of dry tetrahydrofuran. After the reaction mixture had been refluxed for 2 hours, it was cooled and, while cooling with ice, 1.6 ml of water in 10 ml of tetrahydrofuran, 3.2 ml of 2N sodium hydroxide and 3.2 ml of water were successively added dropwise. After refluxing for a short periode of time the resulting precipitate was filtered off and rinsed thoroughly with warm tetrahydrofuran; the filtrate was evaporated under reduced pressure. The resulting crude product was purified by means of flash chromatography over 100 g of silicagel (Merck, grain size 0.040-0.063 mm) using a mixture of ethyl acetate, methanol and concentrated ammonia (93:6.5:0.5) as an eluent. After combining and evaporating the desired fractions, totally 3.6 g (65%) of 2,5-dimethyl-3-(4-methoxyphenyl)piperidine were obtained.

Workup

  1. temperatureAfter the reaction mixture had been refluxed for 2 hours
  2. temperatureit was cooled
  3. additionwere successively added dropwise
  4. temperatureAfter refluxing for a short periode of time the resulting precipitate
  5. filtrationwas filtered off
  6. washrinsed thoroughly with warm tetrahydrofuran
  7. customthe filtrate was evaporated under reduced pressure
  8. customThe resulting crude product was purified by means of flash chromatography over 100 g of silicagel (Merck, grain size 0.040-0.063 mm)
  9. additiona mixture of ethyl acetate, methanol and concentrated ammonia (93:6.5:0.5) as an eluent
  10. customevaporating the desired fractions

Sources & evidence

ORD record
ord-07249fd7573340dd91c12d18a65c413d
Source dataset
uspto-grants-1992_02
Patent number
US05091393

Reaction notes

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