Phenethylamine → HCID 59351595, compound

HRID 1889414Notes

Reaction equation

HRID 1889414 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4]([O:6]C)=O.ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH2:38][CH2:39][NH2:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[I:12][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][CH:10]=1)[NH:1][C:17](=[O:23])[N:40]([CH2:39][CH2:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:4]2=[O:6]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 847811Methyl 2-amino-5-iodobenzoate

Product 1

HCID 59351595HCID 59351595, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (40 mL) of methyl 2-amino-5-iodobenzoate (2.3 g) in methylene chloride were added triphosgene (3.2 g) and triethylamine (3.9 g), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 2-phenylethanamine (3.0 g), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (30 mL), 60% sodium hydride (0.5 g) was added, and the mixture was stirred at 70° C. for 2 hr. The reaction mixture was neutralized with hydrochloric acid (10% methanol solution), insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (2.1 g, 65%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (30 mL)
  6. addition60% sodium hydride (0.5 g) was added
  7. stirringthe mixture was stirred at 70° C. for 2 hr
  8. filtrationwas filtered off
  9. customthe solvent was evaporated under reduced pressure
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-8fff7e39f7e94b8cbc09c3f3e4fecc9d
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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