N-methyl-2-pyrrolidone → 6-Fluorobenzo[b]thiophen-3-amine

HRID 1885317Notes

Reaction equation

HRID 1885317 reaction equation
COC([C:5]1[S:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[NH2:15])=O.CN1CCNCC1.CN1CCCC1=O>O>[NH2:15][C:6]1[C:7]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:8]=2[S:9][CH:5]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 531671-MethylpiperazineHCID 10585280Methyl 3-amino-6-fluoro-1-benzothiophene-2-carboxylate

Product 1

HCID 107971626-Fluorobenzo[b]thiophen-3-amineYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
176 °C

Procedure

A mixture of methyl-6-fluoro-3-aminobenzo[b]thiophene-2-carboxylate (20.1 g), 1-methylpiperazine (13.1 g), and 1-methyl-2-pyrrolidinone (100 ml) was heated at 176° C. for 2 hrs, under nitrogen. The solution was diluted with water (400 ml) and extracted with ether. The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 9.32 g of 3-amino-6-fluorobenzo[b]thiophene.

Workup

  1. extractionextracted with ether
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ca11fa1fc3046df8bfcfcaf20238ff6
Source dataset
uspto-grants-1992_09
Patent number
US05143923

Reaction notes

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