2,2-Dimethyl-N-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-propionamide → 6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-amine

HRID 379375Notes

Reaction equation

CC(C)(C)C([NH:5][C:6]1[CH:7]=[N:8][C:9]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=O>Cl>[CH3:25][N:22]1[CH2:21][CH2:20][N:19]([C:9]2[N:8]=[CH:7][C:6]([NH2:5])=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH:10]=2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 92.5 °C

Procedure

A suspension of 56 g (152 mmol) 2,2-dimethyl-N-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-propionamide in 1300 ml 3 N hydrochloric acid solution was heated to 90-95° C. overnight. The reaction mixture was cooled to room temperature, washed with three 500 ml portions diethyl ether and filtered over celite. The filtrate was diluted with 500 ml water and was adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling. The product was extracted with four 1000 ml portions of dichloromethane. The combined organic layers were washed with 500 ml brine, dried (magnesium sulfate) and evaporated to give 35 g (82%) of the title compound as a light brown oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with three 500 ml portions diethyl ether
filtrationfiltered over celite
additionThe filtrate was diluted with 500 ml water
additionwas adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling
extractionThe product was extracted with four 1000 ml portions of dichloromethane
washThe combined organic layers were washed with 500 ml brine
dry with materialdried (magnesium sulfate)
customevaporated

Sources & evidence

ORD record: ord-6b060a6952c74d6485ed82cd33679751
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297375B1

Reaction notes

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