Aluminium lithium hydride → (Z)-5,6-dihydrodibenzo[b,f]azocine

HRID 1404653Notes

Reaction equation

HRID 1404653 reaction equation
[CH:1]1[C:12]2[CH:11]=[CH: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-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH:1]1[C:12]2[CH:11]=[CH: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 21226445Aluminium lithium hydrideHCID 53780663(Z)-dibenzo[b,f]azocin-6(5H)-one

Product 1

HCID 66710187(Z)-5,6-dihydrodibenzo[b,f]azocineYield 58.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1 (7.4 g, 33.4 mmol) and lithium aluminum hydride (2.494 ml, 66.9 mmol) in anhydrous ether (200 mL) was refluxed for 15 hours. The reaction mixture was quenched by water, filtered, and the filter cake was washed with ether. The filter cake was dispersed in ether (100 mL), stirred for 10 minutes, and filtered. The combined organic layers were dried over MgSO4, solvent was removed under vacuum, and the product purified by chromatography to provide 4.04 g (19.49 mmol, 58%) of 5,6-dihydrodibenzo[b,f]azocine (2). 1H, 7.27-7.23 (m, 1H), 7.2-7.1 (m, 3H), 6.96-6.9 (m, 1H), 6.9-6.8 (m, 1H), 6.65-6.55 (m, 1H), 6.54-6.48 (m, 1H), 6.40 (d, J=8 Hz, 1H), 6.38-6.29 (m, 1H), 4.51 (d, J=6.8 Hz, 2H), 4.2 (br s, 1H); 13C: 147.3, 139.3, 138.3, 134.9, 132.7, 130.3, 129.0, 128.1, 127.8, 127.6, 127.5, 121.8, 118.1, 117.9, 49.6. HRMS (ESI+) calcd for C15H14N [M+H]+ 208.1126. found 208.1120.

Workup

  1. temperaturewas refluxed for 15 hours
  2. customThe reaction mixture was quenched by water
  3. filtrationfiltered
  4. washthe filter cake was washed with ether
  5. additionThe filter cake was dispersed in ether (100 mL)
  6. filtrationfiltered
  7. dry with materialThe combined organic layers were dried over MgSO4, solvent
  8. customwas removed under vacuum
  9. customthe product purified by chromatography

Sources & evidence

ORD record
ord-166aaea786b94824ac3d87b65a6b8439
Source dataset
uspto-grants-2014_12
Patent number
US08912322B2

Reaction notes

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