Aluminium lithium hydride → HCID 21428695, compound

HRID 437560Notes

Reaction equation

HRID 437560 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][C:23]([CH3:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:23]1([CH3:26])[CH:24]=[CH:25][C:20]([O:19][CH:16]2[CH2:15][CH2:14][N:13]([CH2:11][CH2:10][C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:18][CH2:17]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21428698HCID 21428698, compound

Product 1

HCID 21428695HCID 21428695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 4.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-tolyloxy)piperidine in 40 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 2.1 g of lithium aluminum hydride in 60 ml. of tetrahydrofuran. After addition is complete the mixture is stirred and refluxed for 3 hours under nitrogen. After cooling, the excess hydride is carefully destroyed with water. The mixture is filtered, the filter cake is washed with tetrahydrofuran, and the filtrate is concentrated to a colorless oil under reduced pressure. The oil is kept under vacuum for 24 hours and then permitted to stand for several days. The oil slowly solidifies to a white solid. The solid is collected, washed with petroleum ether (b.p. 30°-60°) and recrystallized from an ethanol and water mixture to give white needles of 3-{2-[4-(p-tolyloxy)piperidyl]ethyl}indole, m.p. 115°-117° C.

Workup

  1. additionAfter addition
  2. temperaturerefluxed for 3 hours under nitrogen
  3. temperatureAfter cooling
  4. customthe excess hydride is carefully destroyed with water
  5. filtrationThe mixture is filtered
  6. washthe filter cake is washed with tetrahydrofuran
  7. concentrationthe filtrate is concentrated to a colorless oil under reduced pressure
  8. waitto stand for several days
  9. customThe solid is collected
  10. washwashed with petroleum ether (b.p. 30°-60°)
  11. customrecrystallized from an ethanol and water mixture

Sources & evidence

ORD record
ord-21da2bd5e5a54ebfbdd0a07d1100e04e
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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