3-Aminomethyl-1-N-Cbz-piperidine → HCID 86649870, compound

HRID 2089009Notes

Reaction equation

HRID 2089009 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:13]1>O1CCOCC1.C(N(C(C)C)CC)(C)C>[Cl:9][C:4]1[N:3]=[C:2]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:13]2)[CH:7]=[C:6]([I:8])[CH:5]=1

Participants

5

Reactant 2

HCID 27564883-Aminomethyl-1-N-Cbz-piperidineHCID 117373932,6-Dichloro-4-iodopyridine

Product 1

HCID 86649870HCID 86649870, compound

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2,6-dichloro-4-iodopyridine (1.5 g, 5.5 mmol) and benzyl 3-(aminomethyl)piperidine-1-carboxylate (2.7 g, 11 mmol) in dioxane (10 mL) in a microwave tube was added ten drops of diisopropylethyl amine and sealed. The tube was heated at 150° C. for 72 hours. The reaction mixture was cooled to room temperature and concentrated, the residue was purified by flash chromatography eluting with EtOAc/hexane=1:3 to 1:2 to give the title compound. Yield: 1.0 g (38%). MS (DCI/NH3) m/z 486 (M+H)+.

Workup

  1. customsealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography
  5. washeluting with EtOAc/hexane=1:3 to 1:2

Sources & evidence

ORD record
ord-abe0346bf7fa45fb9798798095619064
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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