Реакция #2122477

Уравнение реакции

Biotin

piperazine

pyridine

→

piperazine biotinamide

Выход 10.0%

Растворители

thionyl chloride

thionyl chloride

Условия реакции

Обработка

1. 1
   Другоеwas removed
2. 2
   Другоеdried down
3. 3
   workup.ADDITIONwas added to the resulting oil
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеthe resulting solid was triturated with 40 mL of MeOH
6. 6
   ФильтрацияThe MeOH soluble material was collected by filtration
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеtriturated with 40 ml of CH2Cl2
9. 9
   ФильтрацияThe CH2Cl2 soluble material was collected by filtration
10. 10
    Концентрированиеconcentrated
11. 11
    Другоеchromatographed on a 1 cm silica column with 2:98 NH4OH
12. 12
    ПромывкаElution
13. 13
    КонцентрированиеThe appropriate fractions were concentrated

Методика

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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