Triethylamine → HCID 25591723, compound

HRID 1404450Notes

Reaction equation

HRID 1404450 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][CH2:20][C:21](Cl)=[O:22].C(N(CC)CC)C>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:21](=[O:22])[CH2:20][CH2:19][C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 1381512554536-91-3

Product 1

HCID 25591723HCID 25591723, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-benzylpiperazine (352 mg, 2 mmol) in dry dichloromethane (6 mL) is cooled in an ice bath, and 3-(furan-2-yl)propionyl chloride (396.5 mg, 2.5 mmol, 1.25 eq) and triethylamine (417 μL, 3 mmol, 1.5 eq) are added. After stirring for 6 hours at room temperature the reaction mixture is diluted with dichloromethane (10 mL). The organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine. After drying over Na2SO4, dichloromethane is removed in vacuo and the crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:2). The fractions containing the 1-(4-benzylpiperazin-1-yl)-3-(furan-2-yl)propan-1-one are collected and the solvent is removed in vacuo to give 497 mg of colorless oil.

Workup

  1. washThe organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine
  2. dry with materialAfter drying over Na2SO4, dichloromethane
  3. customis removed in vacuo
  4. customthe crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:2)
  5. additionThe fractions containing the 1-(4-benzylpiperazin-1-yl)-3-(furan-2-yl)propan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-90848c1cd5194ee2a87a7a3cbe179b05
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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