Aluminium lithium hydride → HCID 12290108, compound

HRID 2035418Notes

Reaction equation

HRID 2035418 reaction equation
O[C:2]1([CH3:18])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=O)[NH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH3:18][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68979461HCID 68979461, compound

Product 1

HCID 12290108HCID 12290108, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

11-Hydroxy-11-methyl-5,11-dihydro-dibenzo[b,e]azepin-6-one (3) (51.6 g 0.22 mol) was added to a suspension of LiAlH4 (33 g, 0.88 mol) in dioxane (850 mL). The reaction mixture was heated to 105° C. After 2.5 h under reflux the reaction mixture was cooled, the excess LiAlH4 was destroyed with aqueous Na2SO4 (55 mL). ethyl acetate (1.81) and Na2SO4 (440 g) were added, the reaction mixture was stirred for 30 min. The solids were filtered off and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=6:4) to give 6,11-dihydro-11-methyl-5H-dibenzo[b,e]azepine (4) (28 g, 61%) Data: (m/z)=210 (M+H)+.

Workup

  1. temperatureAfter 2.5 h under reflux the reaction mixture
  2. temperaturewas cooled
  3. customthe excess LiAlH4 was destroyed with aqueous Na2SO4 (55 mL)
  4. additionethyl acetate (1.81) and Na2SO4 (440 g) were added
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=6:4)

Sources & evidence

ORD record
ord-a9b3e475e1964cfb8f9649543ec82b0f
Source dataset
uspto-grants-2013_11
Patent number
US08575152B2

Reaction notes

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