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

HRID 52570ノート

反応式

HRID 52570 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[K+].CS(OCC1CCCCC1)(=O)=O.Cl>CC(OC)(C)C.O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH:2]([NH2:1])[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

8

反応物 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 195092-PyridinemethanamineHCID 19963751Cyclohexylmethyl methanesulfonateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 97942552-Cyclohexyl-1-(pyridin-2-YL)ethanamine収率 40.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

To 465 g (4.3 moles) of 2-(aminomethyl) pyridine was added with stirring 456 g (4.3 moles) of benzaldehyde. The temperature was increased to 70°-80° C. The mixture was diluted with 2 L of MTBE and the water was removed by stirring the solution with 200 g of sodium sulfate overnight. The mixture was filtered and washed with 2 L of MTBE. To remove the remaining water, 100 g of molecular sieves were added. To the mixture was added 483 g (4.3 moles) potassium t-butoxide in portions followed by 842 g (4.38 moles) of cyclohexylmethyl methanesulfonate. After 10-20 hours, the mixture was hydrolyzed by the addition of 5 L water containing 720 mL of hydrochloric acid. The organic phase was separated and discarded. The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide. The product was extracted with petroleum ether to yield 452 g of crude mine. The amine was purified by vacuum distillation at 88° C. and 0.5 Torr to give 353 g (35%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine.

後処理

  1. temperatureThe temperature was increased to 70°-80° C
  2. customthe water was removed
  3. filtrationThe mixture was filtered
  4. washwashed with 2 L of MTBE
  5. customTo remove the remaining water, 100 g of molecular sieves
  6. additionwere added
  7. waitAfter 10-20 hours
  8. customThe organic phase was separated
  9. washThe aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide
  10. extractionThe product was extracted with petroleum ether
  11. customto yield 452 g of crude mine
  12. distillationThe amine was purified by vacuum distillation at 88° C.

出典と根拠

ORDレコード
ord-23414d0e3584429285234f39214914fa
出典データセット
uspto-grants-1997_04
特許番号
US05616717

反応ノート

読み込み中…