Phenylcarbamate compound and muscle relaxant containing the same
A carbamate and carbamoyl technology, applied in the field of muscle relaxation compositions, can solve problems such as side effects
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preparation Embodiment 1
[0079] Preparation Example 1: Synthesis of 1-(2-chlorophenyl)-trans-1-propene
[0080]
[0081] In a flask, 48 ml of 2-chlorobenzaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47 mol) were dissolved in 600 mL of hexane, and then stirred as the temperature increased. Add 53.6ml of boron trifluoride etherate (BF 3 OEt 2 , 0.42mol). When the reaction was complete, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was washed with anhydrous magnesium sulfate (MgSO 4 ) dehydrated and concentrated. The concentrated residue was purified by silica gel column chromatography to give the title compound (38 g, yield 58%).
[0082] 1 H NMR (400MHz, CDCl 3 )δ1.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.11~7.51(m, 4H)
preparation Embodiment 2
[0083] Preparation Example 2: Synthesis of 1-(2-chlorophenyl)-trans-1-butene
[0084]
[0085]Except for using 3-heptanone instead of 3-pentanone, substantially the same method as described in Preparation Example 1 was performed to obtain the title compound (2.9 g, yield 83%).
[0086] 1 H NMR (400MHz, CDCl 3 )δ1.14(d, J=7.6Hz, 3H), 2.29~2.33(m, 2H), 6.28(dt, J=16Hz, 6.4Hz, 1H), 6.78(d, J=15.6Hz, 1H), 7.13~7.54(m, 4H)
preparation Embodiment 3
[0087] Preparation Example 3: Synthesis of 1-(2-chlorophenyl)-3-methyl-trans-1-butene
[0088]
[0089] Except for using 2,6-dimethyl-heptan-4-one instead of 3-pentanone, substantially the same method as described in Preparation Example 1 was carried out to obtain the title compound (8.0 g, yield 50-90%) .
[0090] 1 H NMR (400MHz, CDCl 3 )δ1.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 7.12 ~7.54(m, 4H)
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