Hydrochloric Acid → N-cyclopentylmethyl-9-anthracenemethylamine

HRID 1678896

Reaction equation

HRID 1678896 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH:15]=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH:17]1([CH2:22][NH2:23])[CH2:21][CH2:20][CH2:19][CH2:18]1.[BH4-].[Na+].Cl>C(O)C>[CH:17]1([CH2:22][NH:23][CH2:15][C:13]2[C:14]3[C:5]([CH:6]=[C:7]4[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]4)=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 695049-AnthracenecarboxaldehydeHCID 80153CyclopentanemethylamineHCID 4311764Sodium borohydride

Product 1

HCID 20353249N-cyclopentylmethyl-9-anthracenemethylamineYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 43.5 g of 9-anthraldehyde, 20.97 g of cyclopentylmethylamine and 150 ml of ethanol is heated under reflux for 1.5 hours. The hot solution of N-cyclopentylmethyl-9-anthracenemethyleneimine so obtained is allowed to cool to 60°, and 8.2 g of sodium borohydride is added in small portions, with stirring, while the temperature is maintained at 55-60°. The mixture is then stirred for another 1.5 hours, concentrated hydrochloric acid (35 ml) is added with cooling, and stirring is continued for 0.5 hour. The mixture is then made basic and extracted with methylene chloride. Removal of the solvent from the dried extracts gives 59.1 g of N-cyclopentylmethyl-9-anthracenemethylamine as an oil; nmr spectrum: τ 1.8-3.1 (m, 9); 5.6 (s, 2), 7.5 (d, 7Hz, 2) and 7.8-9.3 (m, 10).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hours
  3. customThe hot solution of N-cyclopentylmethyl-9-anthracenemethyleneimine so obtained
  4. temperatureto cool to 60°
  5. temperatureis maintained at 55-60°
  6. stirringThe mixture is then stirred for another 1.5 hours
  7. temperaturewith cooling
  8. stirringstirring
  9. extractionextracted with methylene chloride
  10. customRemoval of the solvent from the dried extracts

Sources & evidence

ORD record
ord-71c9fb391f66432c9d27227f781421bd
Source dataset
uspto-grants-1978_03
Patent number
US04077977

Linked notes

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