Dichloromethane → 4-[4-(Propan-2-yl)piperazin-1-yl]aniline

HRID 1011269Notes

Reaction equation

HRID 1011269 reaction equation
C(N1CCN(C2C=CC(N)=CC=2)CC1)CC(C)C.[CH:19]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)([CH3:21])[CH3:20].C(Cl)Cl>CCO.[Pd]>[CH:19]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazineHCID 242791864-(4-Isopentylpiperazin-1-yl)aniline

Product 1

HCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]anilineYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Using the method described above for the synthesis of 4-(4-isopentylpiperazin-1-yl)aniline, treatment of 1-isopropyl-4-(4-nitrophenyl)piperazine (11.0 g, 40.1 mmol) with H2 and 10% Pd/C (1.0 g) at RT in EtOH (150 mL) for 24 h, followed by the addition of DCM (100 mL) to the reaction mixture and stirring for a further 3 h, provided crude 4-(4-isopropylpiperazin-1-yl)aniline (7.6 g, 86% recovery, 99% 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 C13H21N3, 219; [M+H]+ found, 220.

Sources & evidence

ORD record
ord-1a5b43744bda4bcba60f92aaec01dfdf
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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