Morpholine → N-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]morpholine-4-carboxamide

HRID 492760ノート

反応式

HRID 492760 の反応式
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>O1CCCC1.C(OCC)C.CN(C)C=O>[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:27]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[O:28])[CH:6]=1

参加物

8

反応物 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

生成物 1

HCID 57677388N-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]morpholine-4-carboxamide収率 64.8%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylamine (1.00 g) in tetrahydrofuran (50 ml) were added triethylamine (1.12 ml) and phenyl chloroformate (0.906 ml) while stirring in an ice bath, followed by stirring in an ice bath for 1 hr. The reaction mixture was concentrated under a reduced pressure to give a residue, to which N,N-dimethylformamide (16 ml) and morpholine (1.4 ml) were added, followed by stirring at room temperature for 4.5 hrs. The reaction mixture was partitioned between ethyl acetate (150 ml) and water (100 ml). The organic layer was washed with a 1 N aqueous solution of sodium hydroxide, brine, 1 N HCl and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a solid, which was then suspended in diethyl ether (50 ml), filtered, and dried under aeration to provide the titled compound (941 mg, 64.8%) as pale yellow powder.

後処理

  1. stirringby stirring in an ice bath for 1 hr
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto give a residue
  4. stirringby stirring at room temperature for 4.5 hrs
  5. customThe reaction mixture was partitioned between ethyl acetate (150 ml) and water (100 ml)
  6. washThe organic layer was washed with a 1 N aqueous solution of sodium hydroxide, brine, 1 N HCl and brine in this order
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under a reduced pressure
  9. customto give a solid, which
  10. filtrationfiltered
  11. customdried under aeration

出典と根拠

ORDレコード
ord-be8ca12dfe84479bb91fb0452db6a770
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

読み込み中…