Aluminium lithium hydride → HCID 17747058, compound

HRID 268750Notes

Reaction equation

HRID 268750 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CO[C:9](=O)[NH:10][CH2:11][CH2:12][CH:13]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[NH:24]1[C:25]2[C:21](=[C:20]([CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:11][NH:10][CH3:9])[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59831668HCID 59831668, compound

Product 1

HCID 17747058HCID 17747058, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a 0° C. stirring suspension of LiAlH4 (0.062 g, 1.69 mmol) in THF (12 ml) under N2 was added a solution [3-(1H-indol-4-yl)-3-phenyl-propyl]-carbamic acid methylester (V) (0.46 g, 1.5 mmol) in THF (7 ml). The resulting mixture was stirred for 15 minutes at room temperature, after which a suspension of LiAlH4 (0.11 g, 3 mmol) in THF (5 ml) was added. The reaction mixture was then refluxed for about 2.5 hours, cooled to about 0° C., and quenched by addition of freshly ground Na2SO4.10H2O (8 g). The resulting mixture was stirred vigorously for about 30 minutes and filtered with the aid of EtOAc. The filtrate was concentrate and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine (0.30 g, 75% yield). To a 0° C. stirring solution of the above amine (0.24 g, 0.90 mmol) in Et2O (10 ml) was added HCl (2 M in Et2O, 0.5 ml, 1.0 mmol). The resulting precipitate was filtered and washed with water and Et2O. The white solid was dried in vacuo affording [3-(1H-indol-4-yl)-3-phenyl-propyl]-methyl-amine (VI) as a hydrochloride salt, (0.21 g, 78% yield). MS (M+H)=265.

Workup

  1. stirringThe resulting mixture was stirred for 15 minutes at room temperature
  2. additionwas added
  3. temperatureThe reaction mixture was then refluxed for about 2.5 hours
  4. temperaturecooled to about 0° C.
  5. customquenched by addition of freshly ground Na2SO4.10H2O (8 g)
  6. stirringThe resulting mixture was stirred vigorously for about 30 minutes
  7. filtrationfiltered with the aid of EtOAc
  8. concentrationThe filtrate was concentrate
  9. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-ea266b7d43c740cdb334973ea65ba7b0
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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