Pyridine → HCID 18323651, compound

HRID 1251323Notes

Reaction equation

HRID 1251323 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.N1C=CC=CC=1.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 13461-(2-Methoxyphenyl)piperazineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 18323651HCID 18323651, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 1-(2-methoxyphenyl)piperazine (21.34 mmol) and pyridine (25.6 mmol) in 60 mL of dry dichloromethane was added dropwise a solution of 6-bromohexanoyl chloride (23.52 mmol) in 20 mL of dichloromethane at 0° C. under nitrogen. After addition, the mixture was allowed to warm to room temperature and stirred for 1-2 hours. The mixture was quenched with 10% potassium carbonate in water, and extracted with dichloromethane. The organic phase was washed with brine and water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 5% methanol, 0.5% ammonium hydroxide in ethyl acetate to give 1-(2-methoxyphenyl)-4-(6-bromohexanoyl)piperazine (6.00 g, 76%).

Workup

  1. additionAfter addition
  2. customThe mixture was quenched with 10% potassium carbonate in water
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with brine and water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-53add0ddece845e19405d7b9fac9c0f1
Source dataset
uspto-grants-2002_01
Patent number
US06342498B1

Reaction notes

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