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Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate → 3-Pyridinamine, N-methyl-4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-

HRID 379418
Notes
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Reaction equation

HRID 379418 reaction equation
CO[C:3](=O)[NH:4][C:5]1[CH:6]=[N:7][C:8]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].COCCO[AlH2-]OCCOC.[Na+]>ClCCl.C1(C)C=CC=CC=1>[CH3:3][NH:4][C:5]1[CH:6]=[N:7][C:8]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 12167320Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMateHCID 16684438Red-Al

Product 1

HCID 158874123-Pyridinamine, N-methyl-4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-Yield 89.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.5 g (1.4 mMol) [6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-carbamic acid methyl ester in 3.0 ml dichloromethane was added over 10 minutes to a solution of 1.98 ml (6.9 mMol ) Red-Al® (70% in toluene) and 2.5 ml toluene (exothermic, cool with a water bath to avoid temperature to go >50° C.). The reaction mixture was stirred 2 hours at 50° C. in CH2Cl2, extracted with ethyl acetate and cooled to 0° C. 4 ml Aqueous NaOH 1N were carefully (exothermic) added over 15 minutes, followed by 20 ml ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with deionized water and brine, dried (Na2SO4) and concentrated under reduced pressure to yield 0.37 g (89%) methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-amine as an orange resin.

Workup

  1. extractionextracted with ethyl acetate
  2. additionadded over 15 minutes
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with deionized water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81e4a7897b2a401082458def58cdf59a
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06297375B1

Reaction notes

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