(RS)-6-(4-Methyl-piperazin-1-yl)4-o-tolyl-4,5-dihydro-pyridine-3-carboxylic acid methylamide → N-methyl-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide

HRID 380746Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:9][C:8]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[N:7][CH:6]=1)=[O:4]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:1][NH:2][C:3](=[O:4])[C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:9][C:8]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[N:7][CH:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 1.5 g (4.6 mmol) (RS)-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-4,5-dihydro-pyridine-3-carboxylic acid methylamide in 15 ml CHCl3 was treated with 2.3 g (23.0 mmol) MnO2. The black suspension was heated to 65° C., stirred for 3 h at 65° C. and treated again with 2.3 g (23.0 mmol) MnO2, stirred for 3 h and added an other 0.9 g (9.2 mmol) MnO2. The reaction mixture was stirred for 10.5 h at 65° C., treated with 0.9 g (9.2 mmol) MnO2, stirred for 1 h at 65° C. and cooled to r.t. After filtration of the MnO2 the solvent was removed under reduced pressure and the residue purified by chromatography over silica gel (CHCl3:MeOH=4:1) to yield 1.24 g (83.2%) product as a beige foam.

Workup

stirringstirred for 3 h
stirringThe reaction mixture was stirred for 10.5 h at 65° C.
stirringstirred for 1 h at 65° C.
temperaturecooled to r.t
filtrationAfter filtration of the MnO2 the solvent
customwas removed under reduced pressure
customthe residue purified by chromatography over silica gel (CHCl3:MeOH=4:1)

Sources & evidence

ORD record: ord-7b1a7f52ae86403c921d2b44bd9d6275
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303790B1

Reaction notes

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