Triethylamine → 1-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one

HRID 1070927

Reaktionsgleichung

Reaktionsgleichung von HRID 1070927
C1N=CN(C(N2C=NC=C2)=O)C=1.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([OH:24])=O)=[CH:21][C:16]=2[N:15]=[N:14]1.Cl.[NH:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([N:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)=[O:24])=[CH:21][C:16]=2[N:15]=[N:14]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27354581,2,3-Benzothiadiazole-5-carboxylic acidHCID 30848514-Piperidone hydrochloride

Produkt 1

HCID 223974651-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-oneAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

CDI (4.5 g) added to a solution of the benzo[1,2,3]thiadiazole-5-carboxylic acid (5 g) stirring in THF (100 ml) at RT. After 1 hour 4-piperidone hydrochloride (3.7 g) and triethylamine (4.3 ml) were added and the mixture stirred overnight. The resulting mixture was diluted with ethyl acetate, washed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml) and then with saturated brine (200 ml). The organic layer was dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane) to give the product as a yellow oil (2.1 g; MS: APCI+(M+H)262).

Aufarbeitung

  1. washwashed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6e61d136b3e24891bdf2cbdc68f922d8
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903115B2

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