Aluminium lithium hydride → HCID 21428722, compound

HRID 437556Notes

Reaction equation

HRID 437556 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH2:15][CH2:14]2)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:21]1([CH3:26])[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH:16]1[CH2:15][CH2:14][N:13]([CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 214287231-(1H-Indol-3-yl)-2-[4-(2-methylphenoxy)-1-piperidinyl]-1,2-ethanedione

Product 1

HCID 21428722HCID 21428722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.7 g of 1-(indol-3-ylglyoxyloyl)-4-(o-tolyloxy)piperidine in 80 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 4.2 g of lithium aluminum hydride in 120 ml. of tetrahydrofuran. After addition is complete, the mixture is stirred and refluxed for 3 hours under nitrogen. The reaction mixture is then cooled and excess hydride is carefully destroyed with water. The mixture is filtered, the filter cake washed with tetrahydrofuran, and the tetrahydrofuran is removed under reduced pressure to give an oil. The oil is evacuated at about 3 mm. overnight, and then rubbed with a glass rod in the presence of hexane to give a white solid. the solid is recrystallized from a benzene and hexane mixture (charcoal treatment) to give off-white crystals. These crystals are recrystallized from an isopropanol and water mixture to give white flakes of 3-{2-[4-(o-tolyloxy)piperidyl]ethyl}indole, m.p. 88°-90° C.

Workup

  1. additionAfter addition
  2. temperaturerefluxed for 3 hours under nitrogen
  3. temperatureThe reaction mixture is then cooled
  4. customexcess hydride is carefully destroyed with water
  5. filtrationThe mixture is filtered
  6. washthe filter cake washed with tetrahydrofuran
  7. customthe tetrahydrofuran is removed under reduced pressure
  8. customto give an oil
  9. customThe oil is evacuated at about 3 mm
  10. customovernight
  11. customto give a white solid
  12. customthe solid is recrystallized from a benzene and hexane mixture (charcoal treatment)
  13. customto give off-white crystals
  14. customThese crystals are recrystallized from an isopropanol and water mixture

Sources & evidence

ORD record
ord-8476b866c908455eb8c6117435d8c0db
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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