1-BOC-3-Aminopiperidine → HCID 86649852, compound

HRID 390100Notes

Reaction equation

HRID 390100 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1>O>[Cl:9][C:4]1[N:3]=[C:2]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)[CH:7]=[C:6]([I:8])[CH:5]=1

Participants

4

Reactant 2

HCID 5458091-BOC-3-AminopiperidineHCID 117373932,6-Dichloro-4-iodopyridine

Product 1

HCID 86649852HCID 86649852, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,6-dichloro-4-iodopyridine (1 g, 3.65 mmol) and tert-butyl 3-aminopiperidine-1-carboxylate (3.66 g, 18 mmol) in a sealed tube was heated at 120° C. for 3 days. After cooling, the mixture was poured into 100 mL of water. The solid was collected by filtration and purified by flash chromatography on silica gel eluting with ethyl acetate to provide 680 mg of the title compound. Yield: 43%. MS (DCI/NH3) m/z 438 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was collected by filtration
  3. custompurified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-875fa7c4738d456c8760041aec49c964
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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