Benzaldehyde → 2-Cyclohexyl-1-(pyridin-2-YL)ethanamine

HRID 52569

반응식

HRID 52569 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[OH-].[Na+].C1(CBr)CCCCC1.Cl>C(OC)CCC.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:10]([NH2:9])[CH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

참가 물질

9

반응물 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 137636Cyclohexane, (bromomethyl)-

생성물 1

HCID 97942552-Cyclohexyl-1-(pyridin-2-YL)ethanamine수율 43.5%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 12338Butyl methyl ether용매

실험 절차

Under a nitrogen atmosphere, 1.365 kg (12.86 moles) of benzaldehyde was added with stirring and cooling to 1.39 kg (12.86 moles) of 2-(aminomethyl)pyridine maintaining the temperature <50° C. After stirring for 2-4 hours, the mixture was diluted with 13 L oft-butylmethyl ether (MTBE). To the clear solution was added 1.05 kg (27.72 moles) sodium hydroxide (flakes) and 2.375 kg (6.43 moles) of tetrabutylammonium iodide. The suspension was stirred for 2 hrs., then 2.3 kg (12.86 moles) of cyclohexylmethyl bromide was added. The reaction mixture was refluxed for 36-48 hrs. After cooling the mixture, it was diluted with 3 L of water followed by 12 L of 3N hydrochloric acid and stirred for 2-6 hours. The organic phase was separated and discarded. The aqueous phase was washed four times with 3 L of methylene chloride, then basified with 2.5 L of 0.5N ammonium hydroxide solution. The racemic amine was extracted three times with 4 L of methylene chloride, dried over sodium sulfate and concentrated to dryness. The oil product was stirred with 2 L of hexane, filtered and concentrated to yield 1.14 kg (43.5%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine.

후처리

  1. stirringAfter stirring for 2-4 hours
  2. stirringThe suspension was stirred for 2 hrs
  3. temperatureThe reaction mixture was refluxed for 36-48 hrs
  4. temperatureAfter cooling the mixture, it
  5. stirringstirred for 2-6 hours
  6. customThe organic phase was separated
  7. washThe aqueous phase was washed four times with 3 L of methylene chloride
  8. extractionThe racemic amine was extracted three times with 4 L of methylene chloride
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated to dryness
  11. stirringThe oil product was stirred with 2 L of hexane
  12. filtrationfiltered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d4427c5c5c8d42b78d3ed792b788bece
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616717

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