Tetrahydrofuran → N-[2-(3-hydroxy-2-pyridyl)propyl]-isopropylamine

HRID 848442ノート

反応式

HRID 848442 の反応式
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:9]([N:12]=[CH:13]C)([CH3:11])[CH3:10].[Cl-].[NH4+].O1CCC[CH2:18]1>C([Li])CCC.CCCCCC>[OH:8][C:7]1[C:2]([CH:1]([CH3:18])[CH2:13][NH:12][CH:9]([CH3:11])[CH3:10])=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 707192-Methylpyridin-3-olHCID 141371(E)-N-Isopropylacetaldimine

生成物 1

HCID 20565493N-[2-(3-hydroxy-2-pyridyl)propyl]-isopropylamine

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 178418339Butyllithium溶媒

実験手順

To the solution of 10.9 g of 2-methyl-3-hydroxypyridine in 400 ml of tetrahydrofuran, 88 ml of 2.5 molar n-butyllithium in hexane are added dropwise while stirring under nitrogen and keeping the temperature at about 0°. Stirring is continued for 2 hours at 0°-5°, whereupon 0.2 g of isopropyliminoethane are added rapidly and the temperature is maintained at 0°-5°. After stirring the resulting mixture 2 more hours at said temperature, it is poured into 200 ml of saturated aqueous ammonium chloride. The organic layer is separated, evaporated, redissolved in 100 ml of water and the solution extracted 5 times with 50 ml of diethyl ether. The aqueous phase is saturated with sodium chloride, extracted 5 times with 200 ml of methylene chloride, the combined extracts dried, filtered and evaporated. The residue is dissolved in ethanol and the solution neutralized with ethanolic fumaric acid. The resulting suspension is filtered and the residue recrystallized from ethanol, to yield the hemi-fumarate of N-[2-(3-hydroxy-2-pyridyl)propyl]-isopropylamine of Formula II, with R=H, R'=OH and CpH2p±1 =CH(CH3)2, melting at 199°-199.5°.

後処理

  1. customat about 0°
  2. stirringStirring
  3. additionare added rapidly
  4. temperaturethe temperature is maintained at 0°-5°
  5. customThe organic layer is separated
  6. customevaporated
  7. dissolutionredissolved in 100 ml of water
  8. extractionthe solution extracted 5 times with 50 ml of diethyl ether
  9. extractionextracted 5 times with 200 ml of methylene chloride
  10. customthe combined extracts dried
  11. filtrationfiltered
  12. customevaporated
  13. dissolutionThe residue is dissolved in ethanol
  14. filtrationThe resulting suspension is filtered
  15. customthe residue recrystallized from ethanol

出典と根拠

ORDレコード
ord-a62b5765aebe41fd8b6cf29a92254656
出典データセット
uspto-grants-1981_10
特許番号
US04296115

反応ノート

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