Aluminium lithium hydride → HCID 44249494, compound

HRID 1260370Notes

Reaction equation

HRID 1260370 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=O)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1>C1COCC1>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([CH2:16][C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][CH:8]=[CH:9]3)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 63719141Piperazine,1-(1h-indol-5-ylcarbonyl)-4-methyl-

Product 1

HCID 44249494HCID 44249494, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Lithium aluminium hydride (2.4691 mmol, 0.0938 gram) was taken in a 25 mL two necked round bottom flask provided with a condenser, under nitrogen atmosphere. To this (1H-Indol-5-yl)-(4-methylpiperazin-1-yl)methanone (2.0576 mmol, 0.5 grams) (obtained from step (iii)) dissolved in 5 mL of THF was added and refluxed the mass for a period of 2 hours. After the completion of reaction, the reaction mixture was cooled to 25° C. and quenched by addition of ice-cold water slowly, to decompose the excess of LAH. The resultant precipitate of aluminium hydroxide was removed by filtration over hy-flow. THF was distilled off from this emulsion and the concentrate was diluted with water (20 mL), basified with 20% sodium hydroxide solution to pH: 10 and the mixture was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate extracts were then washed with water (2×20 mL), brine 20 mL and dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure to obtain thick syrupy mass. This syrupy compound was purified over silica gel column, eluent being ethyl acetate and triethylamine (0.2 to 1.0%).

Workup

  1. customprovided with a condenser, under nitrogen atmosphere
  2. additionwas added
  3. temperaturerefluxed the mass for a period of 2 hours
  4. customAfter the completion of reaction
  5. customquenched by addition of ice-cold water slowly
  6. customThe resultant precipitate of aluminium hydroxide was removed by filtration over hy-flow
  7. distillationTHF was distilled off from this emulsion
  8. additionthe concentrate was diluted with water (20 mL)
  9. extractionthe mixture was extracted with ethyl acetate (2×20 mL)
  10. washThe combined ethyl acetate extracts were then washed with water (2×20 mL), brine 20 mL
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe volatiles were removed under reduced pressure
  13. customto obtain thick syrupy mass
  14. customThis syrupy compound was purified over silica gel column, eluent

Sources & evidence

ORD record
ord-a7e197fcf2544b39980fcaba1d4d3aec
Source dataset
uspto-grants-2013_06
Patent number
US08470830B2

Reaction notes

Loading…