Piperidine → HCID 10194640, compound

HRID 916930Notes

Reaction equation

HRID 916930 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9](Cl)=[O:10])=[CH:7][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:4]=1.[NH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.N1CCCCC1>C(Cl)Cl.[Cl-].[Na+].O>[N:26]1([NH:25][C:9]([C:8]2[C:3]([O:2][CH3:1])=[N:4][C:5]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:7]=2)=[O:10])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 166581-AminopiperidineHCID 86600270HCID 86600270, compound

Product 1

HCID 10194640HCID 10194640, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-carbonyl chloride (0.08 mmol) from Step B in methylene chloride (1 mL) was added to a solution-of 1-aminopiperidine (containing a few percent of piperidine as an impurity) (0.017 mL, 0.16 mmol) and TEA (0.022 mL, 0.16 mmol) in methylene chloride (0.5 mL). The reaction was stirred at rt for 20 h and was then diluted with brine and extracted twice with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give a mixture of the crude products. These were separated by preparative TLC (5% methanol in methylene chloride) to give N-(piperidin-1-yl)-2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-carboxamide as the lower eluting product. HPLC/MS: 422 (M+1); Rt=3.8 min;

Workup

  1. extractionextracted twice with methylene chloride
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give
  5. customThese were separated by preparative TLC (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-808a74a022014884baaddd5d25d30f32
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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