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Cesium carbonate → Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate

HRID 884639
Notes
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Reaction equation

HRID 884639 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O1CCOCC1>[CH3:12][C:4]1[CH:3]=[C:2]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 54298739Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoateYield 89%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a pressure vessel was added methyl 4-bromo-2-methylbenzoate (500 mg, 2.18 mmol), Dioxane (5.0 mL), Cs2CO3 (1.4 g, 4.36 mmol), and Xantphos (92.0 mg, 0.16 mmol). The mixture was stirred and nitrogen was bubbled into the reaction for 5 min before adding in Palladium(II) acetate (58 mg, 0.08 mmol), and commercially available N-methyl piperazine (0.26 mL, 2.62 mmol). The vessel was then sealed and heated to 100° C. overnight. The reaction was cooled and filtered through celite. The supernatant was then concentrated and column purified (5:95 EtOAc:Hexanes) to give methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate (480 mg, 89% yield).

Workup

  1. customnitrogen was bubbled into the reaction for 5 min
  2. customThe vessel was then sealed
  3. temperatureThe reaction was cooled
  4. filtrationfiltered through celite
  5. concentrationThe supernatant was then concentrated
  6. customcolumn purified (5:95 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-627032fea15145fcb80507eed3c08447
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes