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

HRID 127449
Notes
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Reaction equation

HRID 127449 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 813491-Amino-4-methylpiperazineHCID 205447457-Nitro-1,4-benzodioxane-5-carbonyl chloride

Product 1

HCID 20544699N-(4-methyl-1-piperazinyl)-7-nitro-1,4-benzodioxane-5-carboxamideYield 55.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

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 recystallized 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

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

Sources & evidence

ORD record
ord-15a0016f5e2a4643903fc71c61d06e76
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04255580

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes