Thiophene → HCID 23339052, compound

HRID 26751Notes

Reaction equation

HRID 26751 reaction equation
S1C=CC=C1.[C:6]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][CH2:13]1.[H][H]>[Pd].CO.C(O)C>[CH:6]1([N:12]2[CH2:13][CH2:14][CH:15]([NH:18][C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:24]=3)[CH2:16][CH2:17]2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 8030ThiopheneHCID 8452CyclopentanoneHCID 18374737N-(Piperidin-4-yl)pyrimidin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 23339052HCID 23339052, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

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.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. washThe whole is washed twice with a diluted sodium hydroxide solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-f8d791ed86564f6688485bff2cc5b045
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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