Piperidine → 2-(6-Bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone

HRID 1931385Notes

Reaction equation

HRID 1931385 reaction equation
[Br:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C1COCC1>[Br:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86638120(6-Bromo-pyridazin-3-yloxy)-acetic acid

Product 1

HCID 866381212-(6-Bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

146 mg (0.626 mmol) of (6-bromo-pyridazin-3-yloxy)-acetic acid, 216.5 mg (1.88 mmol) of NEM and 226 mg (0.689 mmol) of TOTU in 10 ml of THF were stirred at room temperature for 15 min, 80 mg (0.94 mmol) of piperidine added, and the reaction mixture stirred at room temperature for 3 h. After evaporation, a sodium hydrogencarbonate solution and ethyl acetate were added to the residue, and the organic phase was separated, washed, dried and evaporated. Yield: 190 mg.

Workup

  1. customAfter evaporation
  2. additiona sodium hydrogencarbonate solution and ethyl acetate were added to the residue
  3. customthe organic phase was separated
  4. washwashed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-fa71df46bec74b05a56501899bcdbb06
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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