Triethylamine → HCID 4137705, compound

HRID 1404460Notes

Reaction equation

HRID 1404460 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.[C:14](Cl)(=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[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 61186Valeryl chlorideHCID 759941-Benzylpiperazine

Product 1

HCID 4137705HCID 4137705, compoundYield 79.9%

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 pentanoyl chloride (301 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 1:1). The fractions containing 1-(4-benzylpiperazin-1-yl)pentan-1-one are collected and the solvent is removed in vacuo to give 416 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 1:1)
  5. additionThe fractions containing 1-(4-benzylpiperazin-1-yl)pentan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b568583abda848c781a8f996088e6243
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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