4-Chloropyridine hydrochloride → 1-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone

HRID 64885ノート

反応式

HRID 64885 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>COCCO>[N:21]1[CH:22]=[CH:23][C:18]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([N:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:5])=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 818524-Chloropyridine hydrochlorideHCID 5587302-(Piperidine-1-carbonyl)aniline

生成物 1

HCID 557541-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone収率 65.8%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒2 回

実験手順

A solution of 2.77 kg 1-(2-aminobenzoyl)piperidine in 16 liters of 2-methoxyethanol was heated until solvent distillation was about to begin (125° C. internal temperature). A solution of 2.1 kg 4-chloropyridine hydrochloride in 21 liters of 2-methoxyethanol was then slowly added over a period of one hour during which 4 liters of distillate was collected. Heating was continued for another hour while 16 liters of distillate was collected. The reaction mixture was concentrated in vacuo, and the thick residue was dissolved in 10 liters of water. Sodium acetate trihydrate (1.85 kg) was added and the solution washed three times with 3 liters of isopropyl acetate and decolorized with activated charcoal. The aqueous solution was made basic (pH>10) by dropwise addition of sodium hydroxide solution. Seeding during the addition generated a precipitate. A small amount of acetic acid was added to lower the pH to 8.5-9, and after 30 minutes of stirring the product was collected, washed with water and air dried to give 2.51 kg of 1-[2-(4-pyridinylamino)benzoyl]piperidine, m.p. 152°-153° C. The latter product was further purified by recrystallization from acetone to give the compound with m.p. 154°-155° C.

後処理

  1. custom(125° C. internal temperature)
  2. customwas collected
  3. temperatureHeating
  4. waitwas continued for another hour while 16 liters of distillate
  5. customwas collected
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. dissolutionthe thick residue was dissolved in 10 liters of water
  8. additionSodium acetate trihydrate (1.85 kg) was added
  9. washthe solution washed three times with 3 liters of isopropyl acetate
  10. additionby dropwise addition of sodium hydroxide solution
  11. additionSeeding during the addition
  12. additionA small amount of acetic acid was added
  13. customwas collected
  14. washwashed with water and air
  15. customdried

出典と根拠

ORDレコード
ord-1a9b87101a5348aba0cbbb1d20907c6f
出典データセット
uspto-grants-1986_09
特許番号
US04610991

反応ノート

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