4-(4-Isopentylpiperazin-1-yl)aniline → HCID 9161559, compound

HRID 1011271Notes

Reaction equation

HRID 1011271 reaction equation
C(N1CCN(C2C=CC(N)=CC=2)CC1)CC(C)C.[CH:19]1([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>[Pd]>[CH:19]1([N:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:32]=[CH:33][C:34]([NH2:37])=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 242791864-(4-Isopentylpiperazin-1-yl)anilineHCID 24279299HCID 24279299, compound

Product 1

HCID 9161559HCID 9161559, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the method described above for the synthesis of 4-(4-isopentylpiperazin-1-yl)aniline, treatment of 1-cyclohexyl-4-(4-nitrophenyl)piperazine (1.0 g, 3.46 mmol) with H2 and 10% Pd/C provided crude 4-(4-cyclohexylpiperazin-1-yl)aniline (0.89 g, 89% recovery, 78% purity as determined by LC/MS analysis @ UV 254 nm detection). The crude product is used in the next step without further purification. LCMS-ESI (m/z): calcd for C16H25N3, 259; [M+H]+ found, 260.

Sources & evidence

ORD record
ord-bd14f9cf9b1d4933924d4c4ffb1f10a2
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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