5,6,11,12-Tetrahydrodibenz[b,f]azocin-6-one → 5,6,11,12-Tetrahydrodibenzo[b,f]azocine

HRID 599506Notes

Reaction equation

HRID 599506 reaction equation
[CH:1]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 801465,6,11,12-Tetrahydrodibenz[b,f]azocin-6-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 6105775,6,11,12-Tetrahydrodibenzo[b,f]azocineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 11,12-dihydro-5H-dibenzo[b,f]azocin-6-one (2.0 g, 8.96 mmol) in dry THF (20 ml) is added dropwise a solution of LiAlH4 (1.0 N in THF, 8.96 ml) over a period of 10 min. After ceasing of gas evolution, the reaction mixture is kept stirring at reflux overnight, then quenched by the addition of water (0.48 ml). The precipitate is filtered off and the filtrate is extracted twice with EtOAc. The combined organic layers are dried over Na2SO4, the solvent is evaporated and the residue recrystallized from boiling hexane to give off white crystals of the title compound (1.35 g) in 72% yield: tR (LC-2) 1.65 min; ESI-MS(+): m/z 210.70 [M+H]+ (calcd 209.29 for C15H15N).

Workup

  1. temperatureat reflux overnight
  2. customquenched by the addition of water (0.48 ml)
  3. filtrationThe precipitate is filtered off
  4. extractionthe filtrate is extracted twice with EtOAc
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. customthe solvent is evaporated
  7. customthe residue recrystallized

Sources & evidence

ORD record
ord-ffb5ce934f784021b5353f7493e157f7
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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