HCID 11362390, compound → HCID 11304555, compound

HRID 1954220Notes

Reaction equation

HRID 1954220 reaction equation
[CH2:1]([N:8]([CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])[C:9](=O)[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]([CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11362390HCID 11362390, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11304555HCID 11304555, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-3-(1H-indol-3-yl)-N-[2-(2-methoxy-phenoxy)-ethyl]-propion-amide in tetrahydrofuran (50 mL) at room temperature was added lithium aluminum hydride (1.8 g). The reaction was heated to reflux for 12 hours then allowed to cool to room temperature. The reaction was quenched with saturated ammonium chloride and the solid precipitates filtered through celite. The solvent was concentrated under vacuum and the product purified by chromatography (5% methanol-methylene chloride) to afford 2.0 g (86%) of product as a yellow oil. MS EI m/e 414 (M+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 hours
  3. customThe reaction was quenched with saturated ammonium chloride
  4. customthe solid precipitates
  5. filtrationfiltered through celite
  6. concentrationThe solvent was concentrated under vacuum
  7. customthe product purified by chromatography (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-7d897359536349e896dc32fac22cb794
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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