Borane → 1-[2-(Pyridin-3-yl)ethyl]piperazine

HRID 586345Notes

Reaction equation

HRID 586345 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.B>C1COCC1>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:17]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 10709719HCID 10709719, compound

Product 1

HCID 223216011-[2-(Pyridin-3-yl)ethyl]piperazineYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Boc-4-[(3-pyridinyl)acetyl]piperazine (8.0 g, 26.2 mmol) was added to a solution of borane.ThF (2.0 M in THF, 39.5 mL, 78.6 mmol) in THF (200 mL) at 0° C. The mixture was heated to reflux for 8 h and cooled to room temperature. The excess borane was quenched with methanol and 3 N HCl. The mixture stirred for 3 h at room temperature, and the solvents were removed under vacuum. The crude product was purified by chromatography (SiO2, 4:1 CH2Cl2:CMA) to provide 1-[2-(3-pyridinyl)ethyl]piperazine (2.82 g, 36%) as a light yellow oil.

Workup

  1. customat 0° C
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 8 h
  4. customThe excess borane was quenched with methanol and 3 N HCl
  5. customthe solvents were removed under vacuum
  6. customThe crude product was purified by chromatography (SiO2, 4:1 CH2Cl2:CMA)

Sources & evidence

ORD record
ord-618a7b0f73c54bb784cee594a96c2086
Source dataset
uspto-grants-2005_08
Patent number
US06936611B2

Reaction notes

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