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

HRID 57804Notes

Reaction equation

HRID 57804 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

Lithiumaluminum 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-c9593268eace46aabd296c24083a8a59
Source dataset
uspto-grants-2016_09
Patent number
US09434747B2

Reaction notes

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