2-Chloro-3-(trifluoromethyl)pyridine → HCID 10111162, compound

HRID 1351502Notes

Reaction equation

HRID 1351502 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.Cl[C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=1>>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:20]2[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:4][CH2:5]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 10111162HCID 10111162, compound

Conditions

Temperature
100 °C

Procedure

A mixture of benzyl 4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, Step 1) (1 g, 4.03 mmol) and 2-chloro-3-trifluoromethylpyridine (0.25 g) was heated to 100° C. for 12 h. The reaction mixture was cooled and partitioned between EtOAc and pH5.2 citrate buffer. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated to give a crude product. Purification by flash column chromatography (5–50% EtOAc hexane) afforded the title compound. M.S (M+1): 394.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between EtOAc and pH5.2 citrate buffer
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent evaporated
  6. customto give a crude product
  7. customPurification by flash column chromatography (5–50% EtOAc hexane)

Sources & evidence

ORD record
ord-ba581f97f79245259d4d5853c8261413
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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