Synthesis methods of lorcaserin derivative and salt thereof
A technology of lorcaserin and a synthesis method, which is applied in the field of synthesis of active pharmaceutical ingredients of slimming drugs, can solve problems such as cumbersome splitting operation steps, and achieves improved splitting efficiency, simple splitting operation, high purity and yield. Effect
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Embodiment 1
[0039]
[0040]Compound 1 (8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, 8-chloro-1-methyl-2,3,4,5-tetrahydro -1H-benzo[d]azepine) (38.00g, 1.0eq), D-dibenzoyl tartaric acid (69.58g, 1.0eq) was dissolved in methanol (228ml), heated to 65°C, and kept for 1.5-2h. Then slowly cool down to 25-30°C for 3-5h, filter with suction, wash the filter cake with a small amount of methanol, collect the filter cake, and dry to obtain the crude product of compound 2 ((R)-8-chloro-1-methyl-2 , 3,4,5-tetrahydro-1H-3-benzazepine D-dibenzoyl tartrate, (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro- 1H-benzo[d]azepine D-(+)-DBTA) (40.92g, ee=96.6%, Yield=38%).
[0041] Dissolve the crude white solid compound 2 obtained above in methanol (210ml), raise the temperature to 65°C and reflux, add water (12.3g) dropwise until clarification, complete the addition in 15 minutes, keep warm for 1-2h after the addition, and cool down to 55°C in 40 minutes , turbid, 2.5-3.5 hours down to room temperatu...
Embodiment 2
[0045]
[0046] Compound 1 (38.00g, 1.0eq), D-dibenzoyl tartaric acid (69.58g, 1.0eq) was dissolved in ethanol (260ml), and the temperature was raised to 78°C. Insulate for 3-4h, slowly cool down to 25-30°C over 3-5h, filter with suction, wash the filter cake with a small amount of ethanol, collect the filter cake, and dry to obtain the crude compound 2 as a white solid (40.8g, ee=95.6%, Yield= 37%).
[0047] Dissolve the crude white solid compound 2 obtained above in ethanol (230ml), raise the temperature to 65°C, add water (13.0g) dropwise until clarification, complete the addition in 15 minutes, keep warm for 1-2h after the addition, and cool down to 55°C in 40 minutes. After 2.5-3.5 hours, the temperature was lowered to 25°C, suction filtered, the filter cake was washed with a small amount of acetone, and the filter cake was collected to obtain pure compound 2 (33.5 g, ee=99.4%, Yield=90.5%).
[0048] Pure compound 2 (37.90g, ee>99%, 1.0eq) was dissolved in a 20% aqueo...
Embodiment 3
[0051]
[0052] Compound 1 (30.00g, 1.0eq), D-(+)-diacetyltartaric acid (35.90g, 1.0eq) was dissolved in acetone (250ml) and heated to 56°C. Insulate for 1.5-2h, slowly cool down to 20-25°C over 3-5h, filter with suction, wash the filter cake with a small amount of acetone, collect the filter cake, and dry to obtain the crude product of compound 4 ((R)-8-chloro-1- Methyl-2,3,4,5-tetrahydro-1H-3-benzazepine D-(+)-diacetyl tartrate, (R)-8-chloro-1-methyl-2,3, 4,5-tetrahydro-1H-benzo[d]azepine(2R,3R)-2,3-diacetoxysuccinic acid) (24g, ee=93%, Yield=36.5%).
[0053] Dissolve the crude white solid compound 4 obtained above in acetone (200ml), raise the temperature to 56°C and reflux, add water (10.0g) dropwise until clarification, complete the addition in 15 minutes, keep warm for 1-2h after the addition, and cool down to 55°C in 40 minutes , turbid, 2.5-3.5 hours down to room temperature 25°C, suction filtration, the filter cake was washed with a small amount of acetone, and th...
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