Reaction #954

Reaction equation

4-(N-tert-butyloxycarbonylaminomethyl) piperidine

N-benzyloxycarbonyl-S-methylisothiourea

→

title product

Yield 37.0%

4-(N-tert-butyloxycarbonylaminomethyl)-1-(N-benzyloxycarbon ylamidino) piperidine

Yield 37.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe mixture was heated at 60°-70° C. for six hours
2. 2
   OtherThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
4. 4
   WashThe organic layer was washed twice with 0.3M KHSO4 and once with brine
5. 5
   DryingThe combined organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   OtherThe crude product was purified by flash chromatography

Procedure

7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60°-70° C. for six hours and left at room temperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3M KHSO4 and once with brine. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using a stepwise gradient of CH2Cl2 /MeOH (100/0, 97/3, 95/5, 90/10) as eluent to yield 5.22 g (37%) of the title product.

Source