tert-Butyl piperazine-1-carboxylate → (8-Methyl-4-quinolyl)piperazine

HRID 333960

Reaction equation

HRID 333960 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2Cl.[N:13]1(C(OC(C)(C)C)=O)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>COCCCOCCCO>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 123263354-Chloro-8-methylquinoline

Product 1

HCID 43840508(8-Methyl-4-quinolyl)piperazineYield 80%

Reagents, catalysts & solvents 1

HCID 669843-(3-Methoxypropoxy)-1-propanolSolvent2×

Conditions

Temperature
140 °C

Procedure

8-Methyl-4-chloroquinoline (355 mg, 2 mmol) was suspended in dipropyleneglycolmonomethylether (4 ml), a solution of tert-butyl piperazine-1-carboxylate (440 mg, 2.4 mmol) in dipropyleneglycolmonomethylether (4 ml) was added and the mixture was stirred at 140° C. overnight and the solvent was evaporated under reduced pressure. The residue was dissolved in a mixture of dichloromethane and trifluoroacetic acid (1:1, 4 ml) and stirred at room temperature for 90 minutes. The mixture was evaporated to dryness under reduced pressure and the residue was dissolved in dichloromethane. The solution was washed with 5% sodium bicarbonate solution and water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) to yield 364 mg of a solid (1.6 mmol, 80%). MS (APCI): m/z=227.9 [M+1]+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of dichloromethane and trifluoroacetic acid (1:1, 4 ml)
  3. stirringstirred at room temperature for 90 minutes
  4. customThe mixture was evaporated to dryness under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washThe solution was washed with 5% sodium bicarbonate solution and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol
  10. additionwith the addition of 1% ammonia)

Sources & evidence

ORD record
ord-b009f21a1158469280fafeb63b31bca4
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

Loading…