2-Chlorobenzoxazole → HCID 22142317, compound

HRID 416651Notes

Reaction equation

HRID 416651 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>CC#N>[N:11]1([C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 22142317HCID 22142317, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 40 mL vial at room temperature, 2-chlorobenzo[d]oxazole (760 mg, 5 mmol) was added to a solution of homopiperazine (2 g, 20 mmol) in CH3CN. The reaction mixture gradually turned into a suspension. Upon standing for additional half an hour, solid was filtered off and the collected filtrate was directly subjected to chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH). 420 mg of the desired product was isolated (MS, M++H=218.1).

Workup

  1. waitUpon standing for additional half an hour
  2. filtrationsolid was filtered off
  3. washthe collected filtrate was directly subjected to chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-23e66f559d99498d9ed6f091d49d9716
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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