Water → N-(4-methyl-1-piperazinyl)-7-nitro-1,4-benzodioxane-5-carboxamide

HRID 1660040

Reaction equation

[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[N+:9]([C:12]1[CH:13]=[C:14]([C:22](Cl)=[O:23])[C:15]2[O:20][CH2:19][CH2:18][O:17][C:16]=2[CH:21]=1)([O-:11])=[O:10].O>C(C(C)=O)C>[CH3:8][N:5]1[CH2:6][CH2:7][N:2]([NH:1][C:22]([C:14]2[C:15]3[O:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)=[O:23])[CH2:3][CH2:4]1

Participants

Conditions

Temperature: 10 °C

Procedure

33 g of 1-amino-4-methylpiperazine were dissolved in 630 ml of methyl ethyl ketone. The mixture was cooled to 10° C. and 61 g of 7-nitro-1,4-benzodioxane-5-carbonyl chloride were introduced by portions. The mixture was stirred for two hours and then the solid was filtered off and washed with 150 ml of methyl ethyl ketone. The obtained product was purified by transformation into the base (M.P.: 212° C.) and recrystallized by treatment with hydrochloric ethanol. 45 g of N-(4-methyl-1-piperazinyl)-7-nitro-1,4-benzodioxane-5-carboxamide were obtained (M.P.: 210° C. with one mole of water). The structure was confirmed by nuclear magnetic resonance and infrared analyses.

Workup

filtrationthe solid was filtered off
washwashed with 150 ml of methyl ethyl ketone
customThe obtained product was purified by transformation into the base (M.P.: 212° C.)
customrecrystallized by treatment with hydrochloric ethanol

Sources & evidence

ORD record: ord-6314867bea52488c908c16beaad34445
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04306072

Linked notes

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