2-Chlorobenzoxazole → 2-(4-Methyl-1-homopiperazinyl)benzoxazole

HRID 1780666Notes

Reaction equation

HRID 1780666 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[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>ClCCl>[CH3:11][N:12]1[CH2:18][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

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 2283491-Methylhomopiperazine

Product 1

HCID 105856212-(4-Methyl-1-homopiperazinyl)benzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.54 g portion of 2-chlorobenzoxazole was dissolved in 5 ml of dichloromethane. Under cooling with ice, to this was added dropwise 2.28 g of N-methylhomopiperazine which had been dissolved in 10 ml of dichloromethane, followed by 1 hour of reaction. The reaction solution was concentrated under a reduced pressure, and the resulting residue was dissolved in 500 ml of dichloromethane, washed with water, 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 1.87 g of the title compound.

Workup

  1. temperatureUnder cooling with ice
  2. customfollowed by 1 hour of reaction
  3. concentrationThe reaction solution was concentrated under a reduced pressure
  4. dissolutionthe resulting residue was dissolved in 500 ml of dichloromethane
  5. washwashed with water
  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-27bf051702b842ba9d8f3b2360f5965e
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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