Benzene → HCID 21162633, compound

HRID 893991

Reaction equation

HRID 893991 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[F:13][C:14]1[CH:23]=[CH:22][C:17]([CH:18]=[CH:19][CH:20]=O)=[CH:16][CH:15]=1.C1C=CC=CC=1>O>[F:13][C:14]1[CH:23]=[CH:22][C:17](/[CH:18]=[CH:19]/[CH2:20][NH:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 83551-NaphthalenemethanamineHCID 533843793-(4-Fluorophenyl)-2-propenal

Product 1

HCID 21162633HCID 21162633, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 10 g of 1-aminomethylnaphthalene, 9.55 g of p-fluorocinnamaldehyde and 150 ml of benzene is heated in a reaction vessel equipped with a water separator, at reflux, until the theoretical amount of water has been separated. The mixture is cooled and evaporated to dryness. 5.78 g of the resulting Schiff's base in 60 ml of methanol, after warming to 50°, is mixed, with vigorous stirring, with 1.51 g of solid NaBH4, portionwise, and the mixture is refluxed for 20 minutes. The resulting mixture may be used as such in the next stage. The title compound can be isolated as an oil, however, by evaporation and dividing the residue between aqueous NaHCO3 solution and chloroform, drying the organic phase and evaporation.

Workup

  1. temperatureis heated in a reaction vessel
  2. customhas been separated
  3. temperatureThe mixture is cooled
  4. customevaporated to dryness
  5. temperature5.78 g of the resulting Schiff's base in 60 ml of methanol, after warming to 50°
  6. additionis mixed, with vigorous stirring, with 1.51 g of solid NaBH4
  7. temperatureportionwise, and the mixture is refluxed for 20 minutes

Sources & evidence

ORD record
ord-e62a19f358374655bd4bc8e37ba8132b
Source dataset
uspto-grants-1981_08
Patent number
US04282251

Linked notes

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