Potassium Hydroxide → 3-(SR)-(4-phenyl piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

HRID 380465

Reaktionsgleichung

Reaktionsgleichung von HRID 380465
C(ONC([N:8]1[CH2:12][CH:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:10]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH2:9]1)=O)C=C.[OH-].[K+].O.NN>C(O)CO.CCOCC>[C:25]1([CH:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH:10]3[CH:11]([C:13]4[CH:17]=[CH:16][S:15][CH:14]=4)[CH2:12][NH:8][CH2:9]3)[CH2:24][CH2:23]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18364907HCID 18364907, Verbindung

Produkt 1

HCID 206944833-(SR)-(4-phenyl piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidineAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 0.19 g (0.47 mmol) of 1-allyloxycarbamoyl-3-(SR)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine, 0.52 g (9.4 mmol) KOH and 0.23 mL (4.7 mmol) of hydrazine hydrate in 5 mL of ethylene glycol was heated at 140° C. for 12 h. The reaction mixture was cooled to rt and diluted with ether. The reaction mixture was washed 3 times with H2O, dried over Na2SO4, filtered and the filtrate was concentrated to give 0.13 g of the title compound. 1H NMR (CDCl3) δ7.22-7.37 (m, 7H), 7.04 (d, 1H, J=4.3 Hz), 3.32-3.39 (m, 2H), Mass Spectrum (CI) m/e=327 (M+1).

Aufarbeitung

  1. washThe reaction mixture was washed 3 times with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4160352e82074c429c6d48e838a20921
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303593B1

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