Iodoethane → 1-{2-[Ethyl-(4-pyridinyl)amino]benzoyl}piperidine

HRID 64891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64891
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:3][CH:2]=1.[NH2-].[Na+].[CH2:24](I)[CH3:25]>CN(C)C=O>[CH2:24]([N:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:11])[CH3:25]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24533Sodium amideHCID 557541-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone

Produkt 1

HCID 137124681-{2-[Ethyl-(4-pyridinyl)amino]benzoyl}piperidineAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 22.4 g of 1-[2-(4-pyridinylamino)benzoyl]piperidine (Example 1b) in 45 ml of dimethylformamide was added dropwise to a suspension of sodium amide (from 4.8 g of 50% oil suspension, washed free of oil) in 115 ml of dimethylformamide. The mixture was stirred for one hour, and then 6.5 g of ethyl iodide was added dropwise. The reaction mixture was stirred for two hours, then filtered and concentrated in vacuo. The residue was partitioned between water and ether and the ether-soluble material recovered (15.2 g). The latter was recrystallized from ethyl acetate--pentane to give 13 g of 1-{2-[ethyl-(4-pyridinyl)amino]benzoyl}piperidine, m.p. 123°-124° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for two hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and ether
  5. customthe ether-soluble material recovered (15.2 g)
  6. customThe latter was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2648ece425c241b29fbe36b13df9c0cc
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610991

Notizen zur Reaktion

Wird geladen…