4-Piperidinecarboxamide → HCID 45275354, compound

HRID 1622362Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1Cl.[NH:9]1[CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11][CH2:10]1.C(N(CC)CC)C>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:9]1[CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 37724-Piperidinecarboxamide

HCID 8471Triethylamine

HCID 8176963-Bromo-4-chloropyridine

Product 1

HCID 45275354HCID 45275354, compoundYield 33.2%

Procedure

General procedure C was followed using 3-bromo-4-chloro-pyridine (0.10 g, 0.52 mmol) and isonipecotamide (67 mg, 0.52 mmol) NMP (2 mL) and triethylamine (0.14 mL, 1.0 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 99:1 to 95:5) to furnish the title compound as a white solid (49 mg, 33%), LC-MS (ESI) Rt 0.80 min, m/z 284 (100%, [M+H]+); m/z (ESI) C11H15BrN3O requires 284.0393 found [M+H]+ 284.0392.

Workup

customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 99:1 to 95:5)

Sources & evidence

ORD record: ord-27ec33924e554be0ab0a253abd241b6e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778925B2

Reaction notes

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