Diisopropylethylamine → 3-Bromo-1-(4-chlorophenyl)piperazine 2,2-dimethylpropan-1-one

HRID 417988

반응식

HRID 417988 반응식
[Br:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].Cl.Cl.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.CN(C=O)C.C(Cl)Cl>[Br:1][CH:20]1[NH:21][CH2:22][CH2:23][N:18]([C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][CH:16]=2)[CH2:19]1.[CH3:2][C:3]([CH3:8])([CH3:7])[CH:4]=[O:5]

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 2719323-Bromo-2,2-dimethylpropanoic acidHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

생성물 1

HCID 866357763-Bromo-1-(4-chlorophenyl)piperazine 2,2-dimethylpropan-1-one수율 29.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

반응 조건

온도
0 °C

실험 절차

3-Bromo-2,2-dimethylpropionic acid (1.50 g, 8.29 mmol) was dissolved in thionyl chloride (10 mL) and DMF (0.1 mL). The reaction mixture was heated at reflux for 1.5 hours and then concentrated in vacuo, The residue was dissolved in DCM (10 mL) and added to a solution of 4-chlorophenyl piperazine dihydrochloride (2.35 g, 8.70 mmol) and DIPEA (5.05 mL, 29.0 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and then concentrated in vacuo. The residue was dissolved in DCM (100 mL) and washed with 10% citric acid solution (50 mL), sat aq NaHCO3 solution (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The resulting residue was purified using normal phase column chromatography (eluting with heptane, followed by a 1:1 mixture of EtOAc:heptane) to give 3-bromo-1-(4-chlorophenyl)piperazine-2,2-dimethyl-propan-1-one (0.87 g, 29.3%) as a yellow solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM (10 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in DCM (100 mL)
  7. washwashed with 10% citric acid solution (50 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified
  11. washeluting with heptane
  12. additionfollowed by a 1:1 mixture of EtOAc

출처 및 근거

ORD 기록
ord-1ddbff1a4f0c4fd78f75d394fac43362
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093248B2

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