4-Piperidinecarboxamide → 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

HRID 1622333Notes

Reaction equation

HRID 1622333 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]=[C:15]([Cl:18])[C:16]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Cl:18])[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 37865313,4,5-Trichloropyridine

Product 1

HCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C (See Example 1) was followed using isonipecotamide (380 mg, 3.0 mmol), 3,4,5-trichloropyridine (600 mg, 3.3 mmol), triethylamine (0.84 mL, 6.0 mmol) and NMP (18 mL). The crude product was purified by flash column chromatography on silica gel (CH2Cl2/EtOH, 95:5-91:9) to furnish the title compound as a white solid (0.676 g, 83%); LC-MS (ESI, 4 min) Rt 1.46 min, m/z 274 (100%, [M+H]+); m/z (ESI) C11H13N3OCl2 requires 273.0436, found [M+H]+ 273.0446.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2/EtOH, 95:5-91:9)

Sources & evidence

ORD record
ord-68afb7e7bfb040e1b8f1c70a59e94649
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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