2-Chlorobenzoxazole → HCID 21090379, compound

HRID 350858Notes

Reaction equation

HRID 350858 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.[Cl:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1>Cl.O1CCOCC1>[ClH:15].[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[N:1]1[CH2:2][CH2:3][CH:4]([NH2:7])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 21090379HCID 21090379, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube reactor was mixed with tert-butyl piperidin-4-ylcarbamate (1.0 g, 5.0 mmol) and 2-chlorobenzoxazole (2.3 g, 15.0 mmol). The reactor was sealed and the tube was heated while stirring at a temperature of 100° C. for 2.0 hours. The tube was cooled to RT and the resulting oily solid was dissolved in 4.0 N HCl in 1,4 dioxane (25 mL). The reaction stirred over 16.0 hours and was concentrated to dryness. The resulting solid was triturated with ether and filtered. The product was washed with ether and dried to give 1.1 g of crude solid.

Workup

  1. customThe reactor was sealed
  2. temperaturethe tube was heated
  3. temperatureThe tube was cooled to RT
  4. stirringThe reaction stirred over 16.0 hours
  5. concentrationwas concentrated to dryness
  6. customThe resulting solid was triturated with ether
  7. filtrationfiltered
  8. washThe product was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-5920ae1f84db405abc9dcd55a734b916
Source dataset
uspto-grants-2007_02
Patent number
US07183290B2

Reaction notes

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