Hydrochloric Acid → 4-(4-Fluorobenzoyl)-1-[2-(2-methoxyanilino)ethyl]piperidine

HRID 2461ノート

反応式

HRID 2461 の反応式
C(O[CH:4](OCC)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)C.Cl.[CH3:25][O:26][C:27]1[C:28]([NH2:33])=[CH:29][CH:30]=[CH:31][CH:32]=1.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CO>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][NH:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH3:25])[CH2:11][CH2:10]2)=[O:20])=[CH:18][CH:17]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 196900081-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine

生成物 1

HCID 196900374-(4-Fluorobenzoyl)-1-[2-(2-methoxyanilino)ethyl]piperidine収率 66.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine (81 mg, 0.25 mmol) was dissolved in THF (3 ml) to which was subsequently added 10% hydrochloric acid (2 ml) at room temperature. After 1 hour of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (5 ml×4) to obtain an orange glutinous material. The thus obtained residue was dissolved in methanol (2 ml) to which were subsequently added o-anisidine (29 μl, 0.25 mmol) and sodium cyanoborohydride (11 mg, 0.166 mmol) at room temperature. After 2 hours of stirring at the same temperature, the reaction solution was mixed with saturated sodium carbonate aqueous solution (10 ml), extracted with ethyl acetate and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=2:1-ether) to obtain 59 mg (66.2%) of the title compound in the form of colorless solid.

後処理

  1. customat room temperature
  2. customthe solvent was removed by evaporation
  3. distillationthe resulting residue was subjected to azeotropic distillation
  4. customto obtain an orange glutinous material
  5. customat room temperature
  6. stirringAfter 2 hours of stirring at the same temperature
  7. extractionextracted with ethyl acetate
  8. washwashed with water and saturated brine
  9. dry with materialThe resulting organic layer was dried on anhydrous sodium carbonate
  10. customthe solvent was removed by evaporation
  11. customthe resulting residue was purified

出典と根拠

ORDレコード
ord-237b1973c5eb44b6bba25ecc54bfc269
出典データセット
uspto-grants-1998_03
特許番号
US05728835

反応ノート

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