Phenethylamine → Benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine

HRID 428547

반응식

HRID 428547 반응식
C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P([C:20]2[C:29]([C:30]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=[C:28]3[C:23](C=CC=C3)=[CH:22][CH:21]=2)C2C=CC=CC=2)=CC=1.[CH2:53]([N:60]1[CH2:65][CH2:64][N:63]([C:66]2[CH:67]=[C:68](Br)[CH:69]=[C:70]3[C:75]=2[N:74]=[CH:73][CH:72]=[CH:71]3)[CH2:62][CH2:61]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C([CH2:84][NH2:85])C1C=CC=CC=1>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH2:30]([N:85]([C:68]1[CH:69]=[C:70]2[C:75](=[C:66]([N:63]3[CH2:64][CH2:65][N:60]([CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH2:61][CH2:62]3)[CH:67]=1)[N:74]=[CH:73][CH:72]=[CH:71]2)[CH3:84])[C:29]1[CH:28]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 4

HCID 1001PhenethylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 184140798-(4-Benzyl-piperazin-1-yl)-6-bromo-quinoline

생성물 1

HCID 20701172Benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine수율 407.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
100 °C

실험 절차

To an oven-dried 25 mL round bottom flask was added Cs2CO3 (1.55 g, 4.76 mmol), BINAP (300 mg, 3 mol %), Pd(OAc)2 (100 mg, 3 mol %) and kept under vacuum overnight. To this reaction vessel under a nitrogen atmosphere was added 8-(4-benzyl-piperazin-1-yl)-6-bromo-quinoline (1.3 g, 3.4 mmol), anhydrous toluene (12 mL) and benzylmethylamine (0.53 mL, 4.1 mmol). The reaction mixture was heated at 100° C. overnight. The cooled reaction mixture was diluted with Et2O (15 mL), filtered to remove solids, washed with EtOAc (10 mL) and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexane) affording 830 mg (59%) of benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine as an orange foam.

후처리

  1. customkept under vacuum overnight
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. customto remove solids
  5. washwashed with EtOAc (10 mL)
  6. concentrationconcentrated
  7. customThe resulting oil was purified by column chromatography (40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-0feb875a3e224eeeb54ad3aa073517b4
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313126B1

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