1,4-Dioxane → 2,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole

HRID 576537Notes

Reaction equation

HRID 576537 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[CH2:17][CH2:18][CH2:19][NH:20][C:21](=O)[C:11]=3[C:10]=2[CH:9]=1.O1CCOC[CH2:24]1>>[CH3:24][N:20]1[CH2:19][CH2:18][CH2:17][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][C:10]=3[C:11]=2[CH2:21]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 21226445Aluminium lithium hydrideHCID 287441949-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one

Product 1

HCID 248990502,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole

Procedure

Lithium aluminum hydride (3 g, 78.95 mmol) was placed in 1,4-dioxane (100 mL) under inert atmosphere and 9-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (3 g, 14.018 mmol) was added, and the mixture heated to reflux for 15 h. The reaction was monitored by TLC. The reaction was quenched with saturated aqueous sodium sulfate at 0° C., and the reaction mixture filtered. The filtrate was dried over anhydrous sodium sulfate and evaporated to dryness to afford solid, which was washed with water followed by EtOAc, and dried to afford 1.25 g of the title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureto reflux for 15 h
  4. customThe reaction was quenched with saturated aqueous sodium sulfate at 0° C.
  5. filtrationthe reaction mixture filtered
  6. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customto afford solid, which
  9. washwas washed with water
  10. customdried

Sources & evidence

ORD record
ord-30c67ae0207c438888410f62a721234f
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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