Phenethylamine → HCID 857477, compound

HRID 361598Notes

Reaction equation

HRID 361598 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:23]([NH2:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.O1CCCC1>[CH2:23]([NH:31][C:6]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=1)=[O:8])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 792226-Chloronicotinic acid

Product 1

HCID 857477HCID 857477, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g of 6-chloro-nicotinic acid in 80 ml of N,N-dimethylformamide and 160 ml of tetrahydrofuran was treated with 10.75 g of 1,1'-carbonyldiimidazole and stirred at room temperature for 4 h. Thereafter, the reaction mixture was treated with 8.76 g of phenethylamine and stirred at 70° C. for a further 2 h. The mixture was cooled to room temperature, evaporated to dryness and the residue was taken up in 200 ml of dichloromethane. The organic phase was washed three times with 50 ml of water each time, dried over sodium sulfate and evaporated to dryness. Recrystallization of the residue from isopropanol yielded 11.9 g of 6-chloro-pyridine-3-carboxylic acid phenethyl-amide as a colorless product, m.p. 115° C.

Workup

  1. stirringstirred at 70° C. for a further 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. customevaporated to dryness
  4. washThe organic phase was washed three times with 50 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customRecrystallization of the residue from isopropanol

Sources & evidence

ORD record
ord-764017f1fafb43e8bc48bb0fafdbb60e
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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