Piperazine → 1-(2-chloro-4-fluorophenyl)piperazine

HRID 386530

반응식

HRID 386530 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[Cl:9].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

참가 물질

7

반응물 4

HCID 4837PiperazineHCID 634876Binap, (A+-)-HCID 27334061-Bromo-2-chloro-4-fluorobenzeneHCID 23676156Sodium t-butoxide

생성물 1

HCID 184231511-(2-chloro-4-fluorophenyl)piperazine

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

A suspension of 1-bromo-2-chloro-4-fluorobenzene (4.19 g, 20 mmoles), piperazine (10.32 g, 120 mmoles), sodium tert-butoxide (2.3 g, 1.5 mmoles), tris(dibenzylideneacetone)dipalladium (366 mg, 0.4 mmoles) and racemic (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (747 mg, 1.2 mmoles) in toluene (2 mL) was heated to 120° C. overnight. The mixture was cooled, filtered and the filtrate concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM) to provide the title compound.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM)

출처 및 근거

ORD 기록
ord-1cf0c06515a543c1bf6dfa10e18a5389
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372841B2

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