Water → HCID 22021847, compound

HRID 1266130Notes

Reaction equation

HRID 1266130 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:16]2[C:17]3[C:23](=O)[NH:22][CH2:21][CH2:20][CH2:19][C:18]=3[N:14]3[C:15]=2[C:10]([CH2:11][CH2:12][CH2:13]3)=[CH:9][CH:8]=1.O.[OH-].[Na+]>O1CCOCC1>[CH:7]1[C:16]2[C:17]3[CH2:23][NH:22][CH2:21][CH2:20][CH2:19][C:18]=3[N:14]3[C:15]=2[C:10]([CH2:11][CH2:12][CH2:13]3)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22021840HCID 22021840, compound

Product 1

HCID 22021847HCID 22021847, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of LiAlH4 in 1,4-dioxane (26 mL) was added 5,6,8,9,10,11-hexahydro-4H,12H-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinolin-12-one (300 mg, 1.25 mmol) under N2 at 20° C. The reaction mixture was refluxed for 15 h. The reaction mixture was cooled in an ice bath and added successively with H2O (0.3 mL), 15% NaOH (0.3 mL) and H2O (0.8 mL). The mixture was stirred for 1 h at 20° C. then filtered. The filtrate was concentrated in vacuo. The residue was dissolved in dilute AcOH and washed with Et2O. The aqueous solution was basified with 1N NaOH. A white solid was precipitated and filtered to yield 5,6,9,10,11,12-hexahydro-4H,8H-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (270 mg, 95%).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. filtrationthen filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in dilute AcOH
  6. washwashed with Et2O
  7. customA white solid was precipitated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-723166aa9d224662a520ed88ded238cf
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

Loading…