Reaction #55029

Reaction equation

hydrogen

thiophene

cyclopentanone

N-(4-piperidinyl)-2-pyrimidinamine

→

N-(1-cyclopentyl-4-piperidinyl)-2-pyrimidinamine

Solvents

methanol

ethanol

Conditions

Workup

1. 1
   Filtrationthe catalyst is filtered off
2. 2
   Otherthe filtrate is evaporated
3. 3
   WashThe whole is washed twice with a diluted sodium hydroxide solution
4. 4
   Otherdried
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue is crystallized from 2,2'-oxybispropane
8. 8
   FiltrationThe product is filtered off
9. 9
   Otherdried

Procedure

To 0.5 parts of a solution of 2 parts of thiophene in 40 parts of ethanol, are added 2 parts of cyclopentanone, 5.5 parts of N-(4-piperidinyl)-2-pyrimidinamine and 120 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in 4-methyl-2-pentanone and a small amount of trichloromethane. The whole is washed twice with a diluted sodium hydroxide solution, dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 2.3 parts of N-(1-cyclopentyl-4-piperidinyl)-2-pyrimidinamine; mp. 118° C.

Source