5-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine → 4-(5-Methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)aniline

HRID 518801ノート

反応式

HRID 518801 の反応式
[CH3:1][O:2][C:3]1[CH2:8][N:7]([CH3:9])[CH2:6][CH2:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH:20]([CH3:22])[CH3:21])[CH:11]=1>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH2:8][N:7]([CH3:9])[CH2:6][CH2:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH:20]([CH3:22])[CH3:21])[CH:11]=1

参加物

4

反応物 1

HCID 866979715-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine

生成物 1

HCID 866979724-(5-Methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)aniline収率 31%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

747 mg of zinc are added to a solution of 500 mg of 5-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine in 8 ml of acetic acid. The reaction medium is stirred for 1 hour at ambient temperature and then filtered on Clarcel. The Clarcel is rinsed with 8 ml of acetic acid, then 10 ml of ethanol and then of ethyl acetate. The filtrate is evaporated under reduced pressure and then the residue is taken up in 10 ml of ethyl acetate, 5 ml of water and 10 ml of a saturated aqueous sodium bicarbonate solution. 20 ml of ethyl acetate are added and the two phases are separated. The aqueous phase is extracted with ethyl acetate (2×10 ml). The combined organic phases are washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under vacuum. The residue is purified on 25 g of silica, elution being carried out with dichloromethane/acetone (100/0 to 95/5), so as to obtain 140 mg of 4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)aniline in the form of a brown oil.

後処理

  1. filtrationfiltered on Clarcel
  2. washThe Clarcel is rinsed with 8 ml of acetic acid
  3. customThe filtrate is evaporated under reduced pressure
  4. addition20 ml of ethyl acetate are added
  5. customthe two phases are separated
  6. extractionThe aqueous phase is extracted with ethyl acetate (2×10 ml)
  7. washThe combined organic phases are washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue is purified on 25 g of silica, elution

出典と根拠

ORDレコード
ord-ba0ac3de143844889a007c7143eb8607
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

読み込み中…