Ammonium formate → 5-Methyl-4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)aniline

HRID 518825Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[C:11]([N+:18]([O-])=O)=[CH:10][C:9]=2[CH3:21])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:21][C:9]1[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[C:11]([CH:10]=1)[NH2:18]

Participants

Conditions

Temperature: 80 °C

Procedure

Two 20 ml tubes each containing a mixture of 614 mg of 1-methyl-4-[2-methyl-4-nitro-5-(propan-2-yloxy)phenyl]piperazine, 185 mg of 10% Pd on carbon and 793 mg of ammonium formate in 10 ml of methanol are microwave-heated at 80° C. (P 6-7 bar) for 5 min. The content of the tubes is combined and filtered on Clarcel. The Clarcel is washed with methanol and the filtrate is concentrated under vacuum. The residue is taken up with 20 ml of ethyl acetate, 2 ml of water and 8 ml of a saturated sodium chloride solution. The aqueous phase is extracted three times with 10 ml of ethyl acetate. The combined organic phases are washed with 10 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under vacuum, so as to obtain 1.053 g of 5-methyl-4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)aniline in the form of a light brown solid.

Workup

filtrationfiltered on Clarcel
washThe Clarcel is washed with methanol
concentrationthe filtrate is concentrated under vacuum
extractionThe aqueous phase is extracted three times with 10 ml of ethyl acetate
washThe combined organic phases are washed with 10 ml of a saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-59aec5fa4746428ca69c626cdecc2a1b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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