反应 #2122477

反应方程式

Biotin

piperazine

pyridine

→

piperazine biotinamide

收率 10.0%

溶剂

thionyl chloride

thionyl chloride

反应条件

后处理

1. 1
   其他was removed
2. 2
   其他dried down
3. 3
   workup.ADDITIONwas added to the resulting oil
4. 4
   浓缩concentrated
5. 5
   其他the resulting solid was triturated with 40 mL of MeOH
6. 6
   过滤The MeOH soluble material was collected by filtration
7. 7
   浓缩concentrated
8. 8
   其他triturated with 40 ml of CH2Cl2
9. 9
   过滤The CH2Cl2 soluble material was collected by filtration
10. 10
    浓缩concentrated
11. 11
    其他chromatographed on a 1 cm silica column with 2:98 NH4OH
12. 12
    洗涤Elution
13. 13
    浓缩The appropriate fractions were concentrated

实验过程

Biotin (0.34 g, 1.4 mmols) was dissolved in 8 mL of neat thionyl chloride. This reaction was allowed to proceed for 5 min before the reaction was placed under vacuum where excess thionyl chloride was removed. The resulting oil was resuspended in 10 mL of CH2Cl2 and dried down. This process was repeated three times in order to drive off excess thionyl chloride. A solution of piperazine (0.54 g, 6.3 mmols) dissolved in 30 mL of pyridine was added to the resulting oil. This solution was stirred overnight, concentrated and the resulting solid was triturated with 40 mL of MeOH. The MeOH soluble material was collected by filtration, concentrated, and triturated with 40 ml of CH2Cl2. The CH2Cl2 soluble material was collected by filtration, concentrated and chromatographed on a 1 cm silica column with 2:98 NH4OH:ethanol as the running solvent. Elution was monitored by TLC where the product displays an Rf of 0.80 with a 33:67 NH4OH:EtOH developing solution. The appropriate fractions were concentrated to give 42.9 mg of the piperazine biotinamide as a white solid in a 10% yield.

来源