Aluminium lithium hydride → [3-(1H-Indol-7-yl)-3-phenyl-propyl]-methyl-amine

HRID 1716630Notes

Reaction equation

HRID 1716630 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][C:12]([NH:14][CH3:15])=O)[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][NH:14][CH3:15])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 598317453-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamide

Product 1

HCID 17747555[3-(1H-Indol-7-yl)-3-phenyl-propyl]-methyl-amineYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of 3-(1H-indol-7-yl)-N-methyl-3-phenyl-propionamide XIX (296 mg, 1.06 mmol) in THF (8 ml) was added a suspension of LiAlH4 (165 mg, 4.24 mmol) in THF (6 ml) at room temperature. The mixture was refluxed for 5 hours, cooled to room temperature, and quenched by slow addition of freshly ground Na2SO4.10H2O (4 g). The resulting mixture was stirred at room temperature for 45 minutes, and the solid was filtered and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH) affording [3-(1H-Indol-7-yl)-3-phenyl-propyl]-methyl-amine XX (182 mg, 65% yield). The free amine (100 mg) was dissolved in Et2O (15 ml) and cooled to 0° C. To the resulting solution was added HCl (1 M in Et2O, 568 μl), and the precipitate was filtered and dried in vacuo to afford the hydrochloride salt. (62 mg, 36% yield). MS (M+H)=265.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customquenched by slow addition of freshly ground Na2SO4.10H2O (4 g)
  3. filtrationthe solid was filtered
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. custompurified via flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-63b375e5100440d18ebfa7e2e7291d65
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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