Phenethylamine → HCID 20394044, compound

HRID 972475Notes

Reaction equation

HRID 972475 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[CH2:16]([NH2:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[N:24][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 29959682-[3-(Dimethylamino)propoxy]benzaldehyde

Product 1

HCID 20394044HCID 20394044, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 32.5 g of 2-(3-dimethylaminopropoxy)benzaldehyde and 18.9 g of phenethylamine in 150 ml of toluene is heated at reflux for 1 hour. After 30 minutes, one mole equivalent of water is collected in a Dean-Stark trap. After cooling to approximately 50° C., the solvent is removed using a rotary evaporator and the oily residue is distilled to give 36.2 g of the title compound, boiling point 165°-167° C. at 0.05 mm of Hg.

Workup

  1. temperatureat reflux for 1 hour
  2. customone mole equivalent of water is collected in a Dean-Stark trap
  3. customthe solvent is removed
  4. customa rotary evaporator
  5. distillationthe oily residue is distilled

Sources & evidence

ORD record
ord-b65475d9d3724a059dd2988084306063
Source dataset
uspto-grants-1977_10
Patent number
US04053471

Reaction notes

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