Oxalic Acid → HCID 131723844, Verbindung

HRID 1271577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271577
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][CH2:15][C@H:16]2[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]2[O:22][CH3:23])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CC(O)C>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][CH2:15][C@H:16]2[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]2[O:22][CH3:23])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Komponenten

4

Edukt 2

HCID 971Oxalic AcidHCID 69419669HCID 69419669, Verbindung

Produkt 1

HCID 131723844HCID 131723844, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-[[[(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)carbonyl]-amino]methyl]-3-methoxy-1-piperidinecarboxylate (0.051 mol) and potassium hydroxide (0.5 mol) in ethanol (200 ml) was stirred and refluxed for 30 hours and then cooled. The solvent was evaporated. The residue was dissolved in water and the solvent was evaporated again. The residue was partitioned between DCM and water. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3)93/7). The pure fractions were collected and the solvent was evaporated, yielding 9 g of (cis)-7-chloro-2,3-dihydro-N-[(3-methoxy-4-piperidinyl)methyl]-1,4-benzodioxin-5-carboxamide (interm. 3-i). Part of interm. (3-i) was dissolved in 2-propanol and converted into the ethanedioic acid salt (1:1). The precipitate was filtered off and dried, yielding 1.2 g of (cis)-7-chloro-2,3-dihydro-N-[(3-methoxy-4-piperidinyl)methyl]-1,4-benzodioxin-5-carboxamide ethanedioate (1:1) (interm. 3-j, mp. 208° C.).

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5002a70c5cc24b97b8f77cb087bc550c
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205410B2

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