Reaktion #53503

Reaktionsgleichung

(2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester

→

1-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-methylaminoethanone

Ausbeute 83.3%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeclose to 45° C
2. 2
   EinengenThe reaction mixture is concentrated to dryness under reduced pressure (5 kPa) at a temperature
3. 3
   Sonstigeclose to 30° C.
4. 4
   SonstigeAfter separating
5. 5
   Waschenthe organic phase is washed with 10 cm3 of water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated to dryness under reduced pressure (1 kPa) at a temperature
9. 9
   Sonstigeclose to 40° C

Vorschrift

A solution of 81 mg of (2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester in 2.5 cm3 of formic acid is stirred for 1 hour at a temperature close to 45° C. The reaction mixture is concentrated to dryness under reduced pressure (5 kPa) at a temperature close to 30° C., taken up in 10 cm3 of ethyl acetate and alkalinized with 10 cm3 of a saturated aqueous sodium bicarbonate solution. After separating after settling out, the organic phase is washed with 10 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 58 mg of 1-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-methylaminoethanone are thus obtained in the form of a beige lacquer [1H NMR spectrum (300 MHz, CDCl3), δ in ppm): from 1.95 to 2.15 (broad unresolved complex, 1H), 2.51 (broad s, 3H), 2.77 (s, 3H), from 3.10 to 3.30 (mt, 4H), 3.49 (broad s, 2H), 3.58 (mt, 2H), from 3.75 to 3.90 (mt, 4H), 4.33 (mt, 2H), 4.49 (s, 1H), 6.83 (broad d, J=8 Hz, 1H), 6.90 (dd, J=8 and 2 Hz, 1H), 7.00 (mt, 1H), from 7.20 to 7.40 (mt, 9H)].

Quelle