Hydrochloric Acid → N-cyclopentylmethyl-9-anthracenemethylamine

HRID 1678896

반응식

HRID 1678896 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 20353249N-cyclopentylmethyl-9-anthracenemethylamine수율 96.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71c9fb391f66432c9d27227f781421bd
출처 데이터셋
uspto-grants-1978_03
특허 번호
US04077977

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