Phenethylamine → HCID 13752947, compound

HRID 542793Notes

Reaction equation

HRID 542793 reaction equation
C(N(CC)CC)C.Cl[CH:9]([NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:10]([Cl:13])([Cl:12])[Cl:11].C(#N)C.[CH2:26]([NH2:34])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[CH2:26]([NH:34][CH:9]([NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:10]([Cl:13])([Cl:12])[Cl:11])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 6342AcetonitrileHCID 8471TriethylamineHCID 20207308HCID 20207308, compound

Product 1

HCID 13752947HCID 13752947, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.7 g of triethylamine was added dropwise to a liquid mixture of 6.0 g of N-(1,2,2,2-tetrachloroethyl)isonicotinamide. 100 ml of acetonitrile and 2.2 g of phenethylamine at a temperature of up to 5° C. The mixture was stirred at room temperature for 2 h and the obtained reaction solution was heated to 50° to 60° C. to carry out the reaction for 3 h, cooled to room temperature and poured in water to precipitate crystals. The crystals were filtered, washed with water, dried and recrystallized from a solvent mixture of n-hexane and ethyl acetate to obtain 3.2 g of N-[1-(phenethylamino)-2,2,2-trichloroethyl]isonicotinamide. m.p. 115° to 117° C.

Workup

  1. customup to 5° C
  2. customthe obtained reaction solution
  3. temperaturewas heated to 50° to 60° C.
  4. customthe reaction for 3 h
  5. temperaturecooled to room temperature
  6. customto precipitate crystals
  7. filtrationThe crystals were filtered
  8. washwashed with water
  9. customdried
  10. customrecrystallized from a solvent mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-0c02a0ac61c647beb99a82af35225829
Source dataset
uspto-grants-1987_04
Patent number
US04659722

Reaction notes

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