Methyl iodide → tert-Butyl 4-{[2-(methoxycarbonyl)phenyl]carbonyl}piperazine-1-carboxylate

HRID 1178122Notes

Reaction equation

HRID 1178122 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].CI.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([OH:31])=[O:30])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C.O>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([O:31][CH3:1])=[O:30])[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27962032-(4-Boc-piperazine-1-carbonyl)benzoic acid

Product 1

HCID 59559652tert-Butyl 4-{[2-(methoxycarbonyl)phenyl]carbonyl}piperazine-1-carboxylateYield 101.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

K2CO3 (383 mg, 2.8 mmol) and CH3I (236 mg, 1.66 mmol) were added, with vigorous stirring, to a solution of 4-(2-carboxy-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (371 mg, 1.1 mmol) in DMF (5 mL) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was then diluted with cold water and the product extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 390 mg of 4-(2-methoxycarbonyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow oil. LC-MS purity: 92.15%.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9dad92e621e74be8aef0a790eee8af3d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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