Methylamine hydrochloride → 3-(1H-Indol-6-yl)-3-(2-methoxy-phenyl)-N-methyl-propionamide

HRID 268778Notes

Reaction equation

HRID 268778 reaction equation
[CH3:1][NH2:2].Cl.C[Al](C)C.CO[C:10](=[O:30])[CH2:11][CH:12]([C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20]>C1C=CC=CC=1>[NH:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH2:11][C:10]([NH:2][CH3:1])=[O:30])[CH:29]=2)[CH:25]=[CH:26]1

Participants

5

Reactant 3

HCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 59831877HCID 59831877, compound

Product 1

HCID 598317553-(1H-Indol-6-yl)-3-(2-methoxy-phenyl)-N-methyl-propionamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a 5° C. stirring suspension of MeNH2.HCl (160 mg, 2.4 mmol) in benzene (2 ml) under N2, in a sealed tube was added dropwise Me3Al (2M in toluene, 1.2 ml, 2.4 mmol). The mixture was stirred at room temperature for 1 hour and a solution of 3-(1H-Indol-6-yl)-3-(2-methoxy-phenyl)-propionic acid methyl ester XXXVII (340 mg, 1.1 mmol) in benzene (10 ml) was added. The resulting mixture was stirred at 90° C. for about 4.5 hours, cooled to room temperature, and the reaction was quenched by slowly adding HCl (1M, 25 ml). The resulting mixture was stirred for 10 minutes, diluted with H2O, and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated to provide 3-(1H-indol-6-yl)-3-(2-methoxy-phenyl)-N-methyl-propionamide XXXVIII (320 mg, 94% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. stirringThe resulting mixture was stirred at 90° C. for about 4.5 hours
  3. temperaturecooled to room temperature
  4. customthe reaction was quenched by slowly adding HCl (1M, 25 ml)
  5. stirringThe resulting mixture was stirred for 10 minutes
  6. additiondiluted with H2O
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with H2O and brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-28d69089503947119b9535bdd06a7991
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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