Water → N-[5-(3-hydroxyphenyl)-2-pyrazinyl]-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide

HRID 1249831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1249831
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)[CH2:4][CH2:3]1.[OH:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31](=O)[O:32]C3C=CC=CC=3)=[N:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[OH:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31]([N:2]3[CH2:7][CH2:6][C:5]4([C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:9](=[O:16])[O:8]4)[CH2:4][CH2:3]3)=[O:32])=[N:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 223806313H-spiro[isobenzofuran-1,4'-piperidin]-3-one hydrochlorideHCID 22660683Phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate

Produkt 1

HCID 22660746N-[5-(3-hydroxyphenyl)-2-pyrazinyl]-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamideAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of spiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (40 mg), phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl)carbamate (51 mg) and triethylamine (119 μL) in chloroform (5 mL) was stirred at 80° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform (20 mL). The organic layer was washed with saturated saline solution (20 mL) and then dried over anhydrous Na2SO4. The concentration of the solvent left a residue, which was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) followed by recrystallization from ethyl ether-hexane to give the subject compound (24 mg) as colorless crystals (melting point 257-259° C.).

Aufarbeitung

  1. extractionextracted with chloroform (20 mL)
  2. washThe organic layer was washed with saturated saline solution (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. waitThe concentration of the solvent left a residue, which
  5. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)
  6. customfollowed by recrystallization from ethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2b88c193fbe04a54b021c5a012bf77ca
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335345B1

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