Piperazine → 4-(Piperazin-1-yl)thieno[3,2-c]pyridine

HRID 653407

Reaction equation

HRID 653407 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)C>[N:11]1([C:2]2[C:7]3[CH:8]=[CH:9][S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 128273124-Chlorothieno[3,2-c]pyridine

Product 1

HCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chlorothieno[3,2-c]pyridine (22.7 g, 0.13 mole) and piperazine (57.7 g, 0.67 mole) were heated in a bomb with a minimum amount of ethanol (50 mL) at 120° for 24 hours. The reaction was cooled, partitioned between dichloromethane and water, and the organic layer was isolated, dried (MgSO4), filtered, and concentrated in vacuo to an oil. Flash chromatography (methylene chloride-10% methanol-1% ammonium hydroxide) of this material gave 16 g (54%) of a golden oil. Treatment of an ethanol solution of the oil with ethanolic HCl followed by recrystallization from ethanol gave the hydrochloride salt as off-white crystals, m.p. 275°-283°.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between dichloromethane and water
  3. customthe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-835e7b028b934112bcad12d39be926bf
Source dataset
uspto-grants-1987_06
Patent number
US04677104

Linked notes

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