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

HRID 428547

反応式

HRID 428547 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0feb875a3e224eeeb54ad3aa073517b4
出典データセット
uspto-grants-2001_11
特許番号
US06313126B1

関連ノート

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