Methylamine hydrochloride → 3-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

HRID 268787Notes

Reaction equation

HRID 268787 reaction equation
[CH3:1][NH2:2].Cl.C[Al](C)C.C(O[C:11](=[O:31])[CH2:12][CH:13]([C:20]1[C:28]([O:29][CH3:30])=[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)C>C1C=CC=CC=1>[CH3:30][O:29][C:28]1[C:20]([CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][C:11]([NH:2][CH3:1])=[O:31])=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2

Participants

5

Reactant 3

HCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 598318913-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 598319013-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a 0° C. suspension of MeNH2.HCl (15.6 mg, 0.231 mmol) in benzene (2 ml) was added Me3Al (2M in toluene, 115 μl, 2.31 mmol). The mixture was stirred at 0° C. for 5 min and at RT for 2 hours after which a solution of 3-(5-methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester XLIX in benzene (4 ml) was added. The reaction mixture was stirred at reflux for 5 hours and at room temperature for 16 hours, and quenched by addition of HCl (0.5 M). The aqueous layer was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to yield crude 3-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide L (37 mg, yellow oil), which was used without purification in the next step.

Workup

  1. additionwas added
  2. customquenched by addition of HCl (0.5 M)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68ffeb121c7d4a24bea3542b31b0b245
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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