Reaction #2122477

Reaction equation

Biotin

piperazine

pyridine

→

piperazine biotinamide

Yield 10.0%

Solvents

thionyl chloride

thionyl chloride

Conditions

Workup

1. 1
   Otherwas removed
2. 2
   Otherdried down
3. 3
   workup.ADDITIONwas added to the resulting oil
4. 4
   Concentrationconcentrated
5. 5
   Otherthe resulting solid was triturated with 40 mL of MeOH
6. 6
   FiltrationThe MeOH soluble material was collected by filtration
7. 7
   Concentrationconcentrated
8. 8
   Othertriturated with 40 ml of CH2Cl2
9. 9
   FiltrationThe CH2Cl2 soluble material was collected by filtration
10. 10
    Concentrationconcentrated
11. 11
    Otherchromatographed on a 1 cm silica column with 2:98 NH4OH
12. 12
    WashElution
13. 13
    ConcentrationThe appropriate fractions were concentrated

Procedure

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.

Source