Methylamine hydrochloride → HCID 59831810, compound

HRID 268772Notes

Reaction equation

HRID 268772 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]=[C:15]([O:19][CH3:20])[CH:14]=1>C1C=CC=CC=1.Cl>[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]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH2:11][C:10]([NH:2][CH3:1])=[O:30])[CH:29]=2)[CH:25]=[CH:26]1

Participants

6

Reactant 3

HCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 59831848HCID 59831848, compound

Product 1

HCID 59831810HCID 59831810, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a 5° C. stirring suspension of MeNH2.HCl (70 mg, 1.04 mmol) in benzene (1 ml) was added Me3Al (2M in toluene, 0.52 ml, 1.04 mmol) dropwise. The reaction mixture was stirred at RT for 1 h and a solution of 3-(1H-indol-6-yl)-3-(3-methoxy-phenyl)-propionic acid methyl ester XXXI (160 mg, 0.52 mmol) in benzene (5 ml) was added. The mixture was stirred at 90° C. for 4 h, cooled to RT, and diluted with HCl (5% in water, 6 ml). The resulting mixture was extracted 3 times with EtOAc. The organic layers were combined, washed with H2O (20 ml) and brine (10 ml), dried over MgSO4, filtered, and concentrated to provide 3-(1H-indol-6-yl)-3-(3-methoxy-phenyl)-N-methyl-propionamide XXXII (160 mg, quantitative yield) as a yellow film.

Workup

  1. stirringThe reaction mixture was stirred at RT for 1 h
  2. stirringThe mixture was stirred at 90° C. for 4 h
  3. temperaturecooled to RT
  4. extractionThe resulting mixture was extracted 3 times with EtOAc
  5. washwashed with H2O (20 ml) and brine (10 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-25a2ac58d1a04d2d85162c4c505450f7
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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