反応 #2122477

反応方程式

Biotin

piperazine

pyridine

→

piperazine biotinamide

収率 10.0%

溶媒

thionyl chloride

thionyl chloride

反応条件

後処理

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

実験手順

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.

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