Cesium carbonate → 1-(6-Methyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine

HRID 880402Notes

Reaction equation

HRID 880402 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=1.C1(P(C2CCCCC2)C2(N(C)C)CC=CC=C2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][C:19]1[N:18]=[C:17]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 804471-(4-Nitrophenyl)piperazineHCID 876016-Chloro-2-picolineHCID 665453382-Dicyclohexylphosphino-2-(N,N-Dimethylamino)Biphenyl

Product 1

HCID 669147631-(6-Methyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 1-(4-nitro-phenyl)-piperazine and 2-chloro-6-methylpyridine, by heating in the presence of palladium (II) acetate, 2-dicyclohexylphospino-2-(N,N′-dimethyl amino)biphenyl and caesium carbonate in a mixture of toluene and THF to give 1-(6-methyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine then catalytic hydrogenation over Raney nickel in methanol.

Sources & evidence

ORD record
ord-7c448c091f054aef9391ce234f22e5a7
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…