Acetic Acid → Benzenemethanamine, N-cyclohexyl-

HRID 53262ノート

反応式

HRID 53262 の反応式
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:8]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 7965CyclohexylamineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 204463Benzenemethanamine, N-cyclohexyl-

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of cyclohexylamine (9.34 g) in methanol (300 ml) was added benzaldehyde (10.0 g) followed by activated 3 Å molecular sieves. After 1 h, sodium cyanoborohydride (7.13 g) was added followed by the dropwise addition of acetic acid (9.2 ml), and the reaction was stirred overnight. The reaction mixture was filtered through hiflo, the solvent removed in vacuo and the resulting white solid was heated under reflux in 5M potassium hydroxide solution for 30 mins. The product was extracted into dichloromethane (3×100 ml) and the combined organic layers were washed with brine (100 ml), dried over sodium sulphate and the solvent was removed in vacuo to give a clear oil. The product was purified by column chromatography (eluting with ethyl acetate) then distillation; bpt=137° C. at 1.0 mbarr. 1H NMR (360 MHz, D6 -DMSO) δ0.94-1.24 (5H, m), 1.48-1.88 (5H, m), 2.32 (1H, m), 2.32 (1H, m), 3.10 (2H, s(b)), 3.72 (2H, s), 7.14-7.40 (5H, m).

後処理

  1. filtrationThe reaction mixture was filtered through hiflo
  2. customthe solvent removed in vacuo
  3. temperaturethe resulting white solid was heated
  4. temperatureunder reflux in 5M potassium hydroxide solution for 30 mins
  5. extractionThe product was extracted into dichloromethane (3×100 ml)
  6. washthe combined organic layers were washed with brine (100 ml)
  7. dry with materialdried over sodium sulphate
  8. customthe solvent was removed in vacuo
  9. customto give a clear oil
  10. customThe product was purified by column chromatography (eluting with ethyl acetate)
  11. distillationdistillation

出典と根拠

ORDレコード
ord-3d3945a9f0564dd4b627cc1c751dfe06
出典データセット
uspto-grants-1997_04
特許番号
US05618812

反応ノート

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