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

HRID 1716658Notes

Reaction equation

HRID 1716658 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-908fc0f2ef2347f0ae62350bd06dc108
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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