1-Methylpiperazine → HCID 69372592, compound

HRID 989326Notes

Reaction equation

HRID 989326 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[S:4][C:3]=1C(OC)=O.CN1CCNCC1>CN1CCCC1=O>[N+:11]([C:10]1[C:5]2[S:4][CH:3]=[C:2]([NH2:1])[C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12695141HCID 12695141, compound

Product 1

HCID 69372592HCID 69372592, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
187.5 °C

Procedure

A mixture of 4.82 g (19.1 mmol) methyl 3-amino-7-nitro-1-benzothiophene-2-carboxylate (WO 9738983), 1-methyl-2-pyrrolidinone (23 mL) and 1-methylpiperazine (6.5 mL) is stirred at 185-190° C. for 4 hours, then cooled to room temperature. The precipitate is filtered, washed with diethyl ether, and dried to give 7-nitro-1-benzothiophen-3-amine (3.3 g, 89%) as a red-brown solid, m.p. 188-191° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate is filtered
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-37e4aef683a44727a1038fccf5246ae9
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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