Benzaldehyde → N-[2-(benzylamino)ethyl]pyridine-3-carboxamide

HRID 463521

反応式

HRID 463521 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

4

反応物 2

HCID 240BenzaldehydeHCID 571799SG 1842

生成物 1

HCID 4242394N-[2-(benzylamino)ethyl]pyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(2-aminoethyl)pyridine-3-carboxamide (26.5 g.) and benzaldehyde (16.35 ml.) in ethanol (220 ml.) was kept for 48 hours. A small quantity of solid was removed by filtration. Sodium borohydride (6.1 g.) was then added to the filtrate which was stirred for 1 hour. Glacial acetic acid was then added cautiously until the solution was neutral. The solution was diluted with water (100 ml.) and basified with 2M sodium hydroxide. The mixture was extracted with ethyl acetate (3×200 ml.) and the extracted washed with saturated brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a column of Florisil (200 g.), eluting with ethyl acetate, to yield N-[2-(benzylamino)ethyl]pyridine-3-carboxamide (29.5 g.) as a pale brown oil.

後処理

  1. customA small quantity of solid was removed by filtration
  2. additionSodium borohydride (6.1 g.) was then added to the filtrate which
  3. additionGlacial acetic acid was then added cautiously until the solution
  4. additionThe solution was diluted with water (100 ml.)
  5. extractionThe mixture was extracted with ethyl acetate (3×200 ml.)
  6. washthe extracted washed with saturated brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by chromatography on a column of Florisil (200 g.)
  10. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-448be9d32d2b459a8a8e1094ca3b22c1
出典データセット
uspto-grants-1985_05
特許番号
US04520027

関連ノート

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