Piperidine → (2-Chloropyridin-4-yl)(piperidin-1-yl)methanone

HRID 460194Notes

Reaction equation

HRID 460194 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:7])[CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2369852-Chloroisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 18771703(2-Chloropyridin-4-yl)(piperidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-chloroisonicotinic acid (1.0 g, 6.35 mmol) in dry CH2Cl2 (50 mL) was added piperidine (1.3 mL, 12.69 mmol), DIEA (2.2 mL, 12.69 mmol), HATU (1.2 g, 3.17 mmol), and EDCI (1.3 g, 6.98 mmol). The mixture was stirred under N2 at RT for 15 h. Solvent was removed and the crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (80:20) gave a white solid. MS m/z: 225.1 (M+H). Calc'd. for C11H13ClN2O-224.07.

Workup

  1. customSolvent was removed
  2. customthe crude compound was purified by chromatography on silica gel
  3. washElution with hexane
  4. customacetone mixture (80:20) gave a white solid

Sources & evidence

ORD record
ord-1fe2fa74508f4cb0a1abcc10cf52f0db
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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