Aluminium lithium hydride → HCID 24782240, compound

HRID 2354569Notes

Reaction equation

HRID 2354569 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9]1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:23]([CH:10]1[CH2:9][N:8]([CH3:6])[CH2:13][CH2:12][N:11]1[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59381926HCID 59381926, compound

Product 1

HCID 24782240HCID 24782240, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyl-4-(1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.39 g, 1.0 mmol) in 30 mL THF was added LiAlH4 (2.5 mL, 1.0 M in THF). The solution was warmed to reflux for 2 hours, then cooled to room temperature and quenched by the slow addition of 50 mL saturated Rochelle's salt. The mixture was extracted with EtOA, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Purification via flash chromatography (94:5:1 DCM/MeOH/NH4OH) afforded 5-(2-benzyl-4-methyl-piperazin-1-yl)-1H-indole (0.21 g, 76%); 1H NMR (300, MHz, CDCl3) δ 8.14 (bs, 1H), 7.37 (J=8.7 Hz, 1H), 7.31 (d, J=2.2 Hz, 1H), 7.26-7.05 (m, 1H), 6.52-6.49 (m, 1H), 3.64-3.71 (m, 1H), 3.31-3.21 (m, 1H), 3.20-3.11 (m, 1H), 2.82-2.70 (m, overlapping, 2H), 2.64 (dd, J=13.2, 7.7, 1H), 2.53-2.36 (m, 3H), 2.30 (s, 3H), MS (+H)=306).

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 2 hours
  3. customquenched by the slow addition of 50 mL saturated Rochelle's salt
  4. extractionThe mixture was extracted with EtOA
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an oil
  10. customPurification via flash chromatography (94:5:1 DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-8c08d2768aa94897bda25810cf63884c
Source dataset
uspto-grants-2010_07
Patent number
US07754721B2

Reaction notes

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