Aluminium lithium hydride → HCID 45273676, compound

HRID 268752Notes

Reaction equation

HRID 268752 reaction equation
CO[C:3](=O)[NH:4][CH2:5][CH2:6][CH:7]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:19]1[C:20]2[C:16](=[CH:15][C:14]([CH:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][CH2:5][NH:4][CH3:3])=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59831838HCID 59831838, compound

Product 1

HCID 45273676HCID 45273676, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(1H-indol-5-yl)-3-phenyl-propyl]-carbamic acid methylester X (0.52 g, 1.7 mmol) in THF (35 ml), LiAlH4 (321 mg, 8.4 mmol) was slowly added. The mixture was refluxed for 1.5 hours, cooled to room temperature, and quenched by slow addition of freshly ground Na2SO4.10H2O. The mixture was stirred at room temperature for 1 hour, filtered through celite with EtOAc. The filtrate was evaporated and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine (XI) as an off-white foam (408 mg, 91% yield). The amine compound was dissolved in a Et2O/THF mixture and HCl (2 M in Et2O, 0.772 ml) was added. The precipitate was filtered, washed with Et2O, and dried affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine hydrochloride salt (371 mg, 80% yield). MS (M+H)=265.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customquenched by slow addition of freshly ground Na2SO4.10H2O
  3. filtrationfiltered through celite with EtOAc
  4. customThe filtrate was evaporated
  5. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-35b502d57a5a457698b729996e07ab24
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

Loading…