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

HRID 333960

반응식

HRID 333960 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 669843-(3-Methoxypropoxy)-1-propanol용매2회

반응 조건

온도
140 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b009f21a1158469280fafeb63b31bca4
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

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