Water → HCID 22110967, compound

HRID 565629Notes

Reaction equation

HRID 565629 reaction equation
[CH3:1][C:2]1([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH2:6][C:5]2[C:7]([CH3:17])=[C:8]([NH:13][C:14](=O)[CH3:15])[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH2:14]([NH:13][C:8]1[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]2[O:3][C:2]([CH3:1])([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:21][CH2:20]3)[CH2:6][C:5]=2[C:7]=1[CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22110983HCID 22110983, compound

Product 1

HCID 22110967HCID 22110967, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)methyl]benzofuran-5-yl]acetamide (0.56 g) in tetrahydrofuran (8 mL) was added 0.11 g of lithium aluminum hydride in small portions under ice-cooling. The mixture was then refluxed for 30 hours. After this reaction mixture was cooled with ice, 0.42 g Hyflo Super-Cel (tradename) and ethyl acetate were added, further followed by addition of water (0.2 mL). The mixture was stirred vigorously and, then, filtered and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to provide 0.35 g of the title compound. Yield 63%.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was then refluxed for 30 hours
  3. additionwere added
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1735eeb7addd4e86b4a53575fc924b10
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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