2,3-Dichloropyridine → HCID 10291987, compound

HRID 1827138Notes

Reaction equation

HRID 1827138 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]([Cl:26])=[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]([Cl:26])=[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 169882,3-DichloropyridineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 10291987HCID 10291987, 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 2,3-dichloropyridine (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): 360.

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-f709966b7e664053965df0793c12cca1
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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