Piperidine → 6-Methoxy-4-piperidino-2,3-dihydrobenzopyran

HRID 3767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 3767
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][CH:13](O)[C:12]=2[CH:18]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][CH:13]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:12]=2[CH:18]=1

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 137128456-Methoxy-3,4-dihydro-2H-1-benzopyran-4-ol

Produkt 1

HCID 137128466-Methoxy-4-piperidino-2,3-dihydrobenzopyran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Methane sulfonyl chloride (14.9 ml) is added dropwise to a stirred solution of the product obtained in Step 1. (31.6 g) and triethylamine (29.3 ml) in methylene chloride (750 ml) cooled to 0° C. under nitrogen. The reaction mixture is stirred at RT for 21/2 hours and cooled to 0° C. Piperidine (175 ml) is added to the cooled reaction mixture and the solution stirred at RT overnight. Sat'd aq. sodium bicarbonate is added to the solution and the mixture is stirred for 30 minutes. The organic layer is separated, washed with sat'd NaCl and dried. The solution is filtered and the filtrate evaporated in vacuo yielding the desired product as its hydrochloride salt.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. stirringthe solution stirred at RT overnight
  3. stirringthe mixture is stirred for 30 minutes
  4. customThe organic layer is separated
  5. washwashed with sat'd NaCl
  6. customdried
  7. filtrationThe solution is filtered
  8. customthe filtrate evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-649ea945dd7e4b54ae14924d504966d6
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04722925

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