Acetic Acid → 1-((4-Bromofuran-2-yl)methyl)-4-methylpiperazine

HRID 2241268Notes

Reaction equation

HRID 2241268 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>O.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[O:5][CH:6]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 27570104-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 160991801-((4-Bromofuran-2-yl)methyl)-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 4-bromofuran-2-carbaldehyde (2.10 g, 12.0 mmol) and THF (10 mL) that was cooled in an ice bath was added 1-methylpiperazine (1.60 ml, 14.4 mmol) dropwise, followed by sodium triacetoxyborohydride (3.81 g, 18.0 mmol) in 3 portions as solid. Acetic acid (0.343 ml, 6.00 mmol) was added, and the reaction was stirred for 18 hours at ambient temperature. The dark mixture was diluted with water (10 mL) and basified to pH>12 by addition of 5N NaOH. The mixture was extracted with diethyl ether (3×50 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo. The resulting black oil (2.10 g, 66%) was carried forward without purification.

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted with diethyl ether (3×50 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting black oil (2.10 g, 66%) was carried forward without purification

Sources & evidence

ORD record
ord-569affb3dc5d46d68f3789f3aab2719a
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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