2-Chlorobenzoxazole → 2-(4-methylpiperazino)-1,3-benzoxazole

HRID 1780654Notes

Reaction equation

HRID 1780654 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.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 531671-Methylpiperazine

Product 1

HCID 37945392-(4-methylpiperazino)-1,3-benzoxazole

Procedure

To 3.08 g of 2-chlorobenzoxazole was added 200 ml of N-methylpiperazine under cooling with ice, followed by 2 hours of reaction at the same temperature. The reaction mixture was concentrated under a reduced pressure, and the resulting residue was dissolved in 200 ml of ethyl acetate, washed with water, dehydrated with MgSO4 and then concentrated to dryness under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) to obtain 2.77 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customfollowed by 2 hours of reaction at the same temperature
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. dissolutionthe resulting residue was dissolved in 200 ml of ethyl acetate
  5. washwashed with water
  6. concentrationconcentrated to dryness under a reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-88fe0893b27541d8bf0119e15a7e8d6b
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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