1-Methylpiperazine → 3-(4-Methylpiperazinyl)-benzoic acid tert-butyl ester

HRID 1058580Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][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)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-benzoic acid tert-butyl ester (6.7 g, 26 mmol), N-methyl piperizine (3.4 ml, 31.2 mmol), sodium t-butoxide (3.5 g, 36.4 mmol). 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.12 g, 0.195 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.067 g, 0.065 mmol) were combined in toluene (200 ml), then was heated to 80 degrees C. Argon gas was then bubbled through the solution for 5 minutes. The reaction mixture was heated and stirred for 5 h. The reaction was then cooled to RT, concentrated in vacuo, and chromatographed (silica gel, 4% MeOH: CH2Cl2) to yield the title compound (4.12 g, 58%).

Workup

customArgon gas was then bubbled through the solution for 5 minutes
temperatureThe reaction mixture was heated
temperatureThe reaction was then cooled to RT
concentrationconcentrated in vacuo
customchromatographed (silica gel, 4% MeOH: CH2Cl2)

Sources & evidence

ORD record: ord-9b37e39ecab1475aac3675a273f11e84
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518267B1

Reaction notes

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