Acetic Acid → 4-(6-Chloronaphthalene-2-sulfonyl)-1-{ethyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

HRID 2086285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086285
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[BH4-].[Na+].[C:37](O)(=O)[CH3:38]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([N:21]([CH2:37][CH3:38])[CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 178254104-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

Produkt 1

HCID 227271194-(6-Chloronaphthalene-2-sulfonyl)-1-{ethyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

Versuchsvorschrift

(Method B) 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (14 g) was dissolved in acetic acid (160 ml) and the reaction mixture was treated portionwise with sodium borohydride (11.36 g) while keeping the temperature at 20° C., and then stirred at room temperature for 15 hours. The reaction mixture was concentrated and the residue was made alkaline by adding an aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue obtained was crystallized from ethanol to obtain the title compound (12.96 g) as colorless crystals.

Aufarbeitung

  1. customat 20° C.
  2. concentrationThe reaction mixture was concentrated
  3. additionby adding an aqueous solution of sodium hydroxide
  4. extractionextracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1c87c4d01b5a426abb3273c9e1d2896a
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723722B1

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