4-Aminopyridine → HCID 12822549, compound

HRID 1105679Notes

Reaction equation

HRID 1105679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][C:13](=[O:15])[O:12][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C1(C)C(C)=CC=CC=1.CS(O)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10](=[O:12])[N:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:13](=[O:15])[CH2:14]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 6395Methanesulfonic Acid2×HCID 7237O-XyleneHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 12822549HCID 12822549, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 22.4 g of 3-(p-chlorophenyl)-glutaric anhydride, 10.3 g of 4-aminopyridine, 350 ml of xylene and 1.5 g of methane sulfonic acid is refluxed on a water separator while stirring for 4 days. After the first day an additional 0.5 g of methane sulfonic acid is added and the hot solution is finally decanted from some gummy material. The crystals formed on cooling are filtered off, triturated with hot ethanol, cooled, filtered off again and dried to yield the 4-(p-chlorophenyl)-1-(4-pyridyl)-piperidin-2,6-dione melting at 204°-206°.

Workup

  1. customThe starting material is prepared
  2. customthe hot solution is finally decanted from some gummy material
  3. customThe crystals formed
  4. temperatureon cooling
  5. filtrationare filtered off
  6. customtriturated with hot ethanol
  7. temperaturecooled
  8. filtrationfiltered off again
  9. customdried

Sources & evidence

ORD record
ord-dcc7aff39aff4299ad27923d98e09079
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

Loading…