1,4-Dioxane hydrochloride → 2-(4-Aminopiperidin-1-yl)-6-chloroisonicotinamide hydrochloride

HRID 2233861Notes

Reaction equation

HRID 2233861 reaction equation
Cl.O1CCOCC1.[NH2:8][C:9]([C:11]1[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[CH:12]=1)=[O:10]>>[ClH:17].[NH2:24][CH:21]1[CH2:20][CH2:19][N:18]([C:13]2[CH:12]=[C:11]([CH:16]=[C:15]([Cl:17])[N:14]=2)[C:9]([NH2:8])=[O:10])[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86608240tert-Butyl 1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-ylcarbamate2×

Product 1

HCID 866082552-(4-Aminopiperidin-1-yl)-6-chloroisonicotinamide hydrochlorideYield 211.9%

Procedure

4 N HCl/Dioxane solution (6 ml) was added to tert-butyl 1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-ylcarbamate (Intermediate 16, 100 mg, 0.282 mmol). The mixture was stirred at room temperature for 90 minutes. The solvent was removed in vacuo and the anhydrous diethylether (25 ml) was added. The solvent was removed in vacuo and light yellow solid that resulted was dried under vacuum for several hours to give the title compound as an off-white solid (87 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe anhydrous diethylether (25 ml) was added
  3. customThe solvent was removed in vacuo and light yellow solid
  4. customthat resulted
  5. customwas dried under vacuum for several hours

Sources & evidence

ORD record
ord-010a6720b8aa45399fc14b563c0b0bfa
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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