Triethylamine → HCID 21701631, compound

HRID 1596226Notes

Reaction equation

HRID 1596226 reaction equation
Cl.Cl.[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH2:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].C(N(CC)CC)C.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>ClCCl.C(OCC)(=O)C>[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH:12][C:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)=[O:26])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 21701657HCID 21701657, compound

Product 1

HCID 21701631HCID 21701631, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-acetyl-4-aminopiperazine dihydrochloride (250 mg) and triethylamine (0.65 ml) in dichloromethane (9 ml) was added 2-thiophenecarbonyl chloride (0.19 ml) at 0° C. The mixture was stirred at ambient temperature for 1 hour, diluted with ethyl acetate and washed with water (×2). The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and ethyl acetate (1:10) to give crystals. Recrystallization from ethanol gave N-(4-acetyl-1-piperazinyl)thiophene-2-carboxamide (256 mg).

Workup

  1. washwashed with water (×2)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with a mixture of methanol and ethyl acetate (1:10)
  7. customto give crystals
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7c1a1215a3f44f5190c7441f03bb2fb1
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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