Isobutyraldehyde → 1-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]-4-isobutylpiperazine

HRID 1058836

Reaktionsgleichung

Reaktionsgleichung von HRID 1058836
C(O[BH3-])(=O)C.[Na+].[CH:7](=O)[CH:8]([CH3:10])[CH3:9].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[N:20]2[CH2:23][C:22](=[CH:24][S:25]([CH2:28][C:29]3[CH:30]=[C:31]([N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:32]=[CH:33][CH:34]=3)(=[O:27])=[O:26])[CH2:21]2)=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([C:41]2[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=2)[N:20]2[CH2:21][C:22](=[CH:24][S:25]([CH2:28][C:29]3[CH:30]=[C:31]([N:35]4[CH2:40][CH2:39][N:38]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:37][CH2:36]4)[CH:32]=[CH:33][CH:34]=3)(=[O:26])=[O:27])[CH2:23]2)=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 6561IsobutyraldehydeHCID 516892Sodium BicarbonateHCID 23670382SodiumacetoxyborohydrideHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

Produkt 1

HCID 696356841-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]-4-isobutylpiperazineAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

32 mg of sodium acetoxyborohydride and then 22 mg of isobutyraldehyde are successively added, at a temperature close to 20° C., to a solution of 54.25 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine in 2 cm3 of 1,2-dichloroethane. After stirring for 4 hours at a temperature close to 20° C., 3 cm3 of dichloromethane and 2 cm3 of a saturated aqueous sodium bicarbonate solution are added to the reaction medium. After separating after settling out, the organic [lacuna] is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 63 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]-4-isobutylpiperazine are thus obtained in the form of a beige lacquer [1H NMR spectrum (400 MHz, CDCl3), δ in ppm): 0.92 (d, J=7 Hz, 6H), 1.82 (mt, 1H) 2.14 (d, J=8 Hz, 2H), 2.54 (t, J=5.5 Hz, 4H), 2.75 (s, 3H), 3.18 (t, J=5.5 Hz, 4H), 3.81 (mt, 2H), 4.32 (mt, 2H), 4.49 (s, 1H), 6.78 (d, J=8 Hz, 1H), 6.89 (dd, J=8 and 2.5 Hz, 1H), 6.97 (broad s, 1H), from 7.15 to 7.30 (mt, 5H), 7.32 (d, J=8 Hz, 4H)].

Aufarbeitung

  1. customclose to 20° C.
  2. customAfter separating
  3. dry with materialthe organic [lacuna] is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  6. customclose to 40° C

Quellen und Nachweise

ORD-Eintrag
ord-6e3cac1bf7454b7d927ba084a75f324d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518264B2

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