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

HRID 428547

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

customkept under vacuum overnight
customThe cooled reaction mixture
filtrationfiltered
customto remove solids
washwashed with EtOAc (10 mL)
concentrationconcentrated
customThe resulting oil was purified by column chromatography (40% EtOAc/hexane)

Sources & evidence

ORD record: ord-0feb875a3e224eeeb54ad3aa073517b4
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313126B1

Linked notes

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