4-(Piperidin-1-yl)aniline → n-[4-(1-Piperidinyl)phenyl]benzo[g]quinolin-4-amine

HRID 650531Notes

Reaction equation

HRID 650531 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.CC(C)([O-])C.[Na+]>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:19]1([C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:2]3[C:11]4[C:6](=[CH:7][C:8]5[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=5[CH:10]=4)[N:5]=[CH:4][CH:3]=3)=[CH:26][CH:27]=2)[CH2:20][CH2:21][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 3

HCID 4135014-(Piperidin-1-yl)anilineHCID 217125854-Bromobenzo[g]quinolineHCID 23676156Sodium t-butoxide

Product 1

HCID 2832014n-[4-(1-Piperidinyl)phenyl]benzo[g]quinolin-4-amineYield 77.5%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

4-Bromobenzo[g]quinoline (7a) (140 mg, 0.54 mmol), 4-(I-piperidino)aniline (115 mg, 1.2 equivalents), tris(dibenzylideneacetone)dipalladium (Pd2(dbba)3, (10 mg, 0.02 equivalents), 1,1′-bis(diphenylphosphino)ferrocene (DPPF, 12 mg, 0.04 equivalents) and sodium t-butoxide (73 mg, 1.4 equiv) in 5 mL of dry toluene were refluxed under a nitrogen atmosphere until observed complete by TLC (approximately 1 h). The mixture was concentrated in vacuo and purification by flash chromatography (gradient: 5 50:50:2 to 60:40:2 hexane:EtOAc:Et3N) provided 148 mg of clean N-[4-(1-piperidinyl)phenyl]benzo[g]quinolin-4-amine (8) (77% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo and purification by flash chromatography (gradient: 5 50:50:2 to 60:40:2 hexane:EtOAc:Et3N)

Sources & evidence

ORD record
ord-4533dcacc6934d90bf2e9b872afc1ac9
Source dataset
uspto-grants-2001_08
Patent number
US06274596B1

Reaction notes

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