Diethyl Ether → HCID 57162630, compound

HRID 1077370Notes

Reaction equation

HRID 1077370 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1[CH2:11][CH2:10][CH2:9][CH2:8]1.C[N:13]1[C:25]2[CH:24]([NH:26][C:27](=O)C3C=CC=CC=3)[CH2:23][CH2:22][CH2:21][C:20]=2[C:19]2[C:14]1=[C:15]([F:36])[CH:16]=[C:17]([F:35])[CH:18]=2.C(O[CH2:41][CH3:42])(=O)C.[CH3:43]COCC>O>[CH2:8]([CH2:27][NH:26][CH:24]1[CH2:25][C:20]2[C:19]3[C:14](=[C:15]([F:36])[CH:16]=[C:17]([F:35])[CH:18]=3)[NH:13][C:21]=2[CH2:22][CH2:23]1)[C:9]1[CH:42]=[CH:41][CH:43]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86733494HCID 86733494, compound

Product 1

HCID 57162630HCID 57162630, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 1.2 g. of lithium aluminum hydride in 60 ml. of dry tetrahydrofuran was added dropwise a solution of 4.6 g. of 3-(N-methylbenzamido-6,8-difluoro-1,2,3,4-tetrahydrocarbazole in 60 ml. of dry tetrahydrofuran and when addition was complete, the mixture was refluxed for forty minutes. Ethyl acetate (15 ml.) was added, followed by 10 ml. of wet ether and, finally 5 ml. of water. The mixture was filtered and the filtrate was evaporated to dryness to give, after recrystallizations from cyclohexane and then isopropyl alcohol, 2.9 g. of 3-(benzylmethylamino)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole, m.p. 137°-139°C. A solution of 0.85 g. of this free base was treated in acetonitrile with 0.11 ml. of methyl iodide, and the solution was warmed on a steam bath for 15 minutes, cooled, and the resulting crystals were collected by filtration to give 0.65 g. of 3-(benzylmethyl-amino)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole methiodide, m.p, 235°-236°C.

Workup

  1. temperaturethe mixture was refluxed for forty minutes
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customto give
  5. customafter recrystallizations from cyclohexane
  6. additionof this free base was treated in acetonitrile with 0.11 ml
  7. temperatureof methyl iodide, and the solution was warmed on a steam bath for 15 minutes
  8. temperaturecooled
  9. filtrationthe resulting crystals were collected by filtration
  10. customto give 0.65 g

Sources & evidence

ORD record
ord-5759794d6c87434a9068b76567655a8a
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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