2-Chlorobenzoxazole → HCID 22142317, compound

HRID 1780670Notes

Reaction equation

HRID 1780670 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:9]1[O:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1>CN(C=O)C>[N:1]1([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

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

Product 1

HCID 22142317HCID 22142317, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 978 mg portion of homopiperazine was dissolved in 3 ml of DMF. Under cooling with ice, 500 mg of 2-chloro-benzoxazole was added to the thus prepared solution, and the reaction was carried out for 1 hour at the same temperature and then for 24 hours at room temperature. The reaction solution was concentrated under a reduced pressure, and the resulting residue was dissolved in 200 ml of ethyl acetate, washed with sodium hydrogencarbonate aqueous solution (pH 8) and water in that order, dehydrated with sodium sulfate and then concentrated under a reduced pressure. Thereafter, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to obtain 540 mg of the title compound.

Workup

  1. additionwas added to the thus prepared solution
  2. waitfor 24 hours at room temperature
  3. concentrationThe reaction solution was concentrated under a reduced pressure
  4. dissolutionthe resulting residue was dissolved in 200 ml of ethyl acetate
  5. washwashed with sodium hydrogencarbonate aqueous solution (pH 8) and water in that order
  6. concentrationconcentrated under a reduced pressure
  7. customThereafter, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a01cd52fe90c49c9820443c08191cbd2
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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