4-Piperidinecarboxamide → HCID 45275020, compound

HRID 1622342Notes

Reaction equation

HRID 1622342 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 27360813,4-Dichloropyridine

Product 1

HCID 45275020HCID 45275020, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using isonipecotamide (43 mg, 0.34 mmol), 3,4,dichloropyridine (50 mg, 0.34 mmol), triethylamine (0.14 mL, 1.0 mmol) and NMP (1.5 mL). The crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1) to furnish the title compound as a colourless oil (18 mg, 22%), m.p. 210-212° C.; umax (CHCl3)/cm−1 2360, 2342, 1653, 1581 1382, 1223, 1135, 1041; m/z (ESI) C11H15ClN3O requires 240.0898, found [M+H]+ 240.0899.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-50b77459d3294b4aa6f73bf91209c96f
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…