Aluminium lithium hydride → [3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine

HRID 268790Notes

Reaction equation

HRID 268790 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C:14]([NH:16][CH3:17])=O)=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:14][NH:16][CH3:17])=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 598317653-(7-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

Product 1

HCID 59831752[3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(7-methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide LV (0.315 mmol) in THF (3 ml) was added a suspension of LiAlH4 (46.6 mg, 1.26 mmol) in THF (4 ml). The resulting mixture was stirred at 0° C. for 5 minutes, at reflux for 5 hours, then cooled to room temperature, and additional suspension of LiAlH4 (46.6 mg, 1.26 mmol) in THF (4 ml) was added. The reaction was refluxed for additional 45 minutes, cooled to 0° C. and freshly ground Na2SO4.10H2O (1 g) was added. The mixture was stirred at room temperature over the weekend. The solid was filtered and washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) to provide the amine compound LVI as a yellow film (37 mg). The free amine was dissolved in Et2O (3 ml), cooled to 0° C., and HCl (1 M in Et2O, 126 μl) was added. The precipitate was filtered affording the hydrochloride salt of [3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-propyl]-methyl-amine LVI as an off-white hygroscopic powder. MS (M+H)=295.

Workup

  1. temperatureat reflux for 5 hours
  2. temperaturecooled to room temperature
  3. additionwas added
  4. temperatureThe reaction was refluxed for additional 45 minutes
  5. temperaturecooled to 0° C.
  6. stirringThe mixture was stirred at room temperature over the weekend
  7. filtrationThe solid was filtered
  8. washwashed with EtOAc
  9. concentrationThe filtrate was concentrated
  10. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-5a99f06d95dc413185de882509253b18
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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