Water → Ethyl 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylate

HRID 704416Notes

Reaction equation

HRID 704416 reaction equation
Br[CH2:2][CH2:3][C:4]([CH3:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5].[N:13]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH3:5][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:12])[CH2:3][CH2:2][N:16]1[CH2:15][CH2:14][N:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 244007(4-Bromo-2-methylbutan-2-yl)benzene

Product 1

HCID 14649429Ethyl 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylateYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-3-methyl-3-phenylbutane (0.73 g), ethyl piperazinecarboxylate (0.51 g) and anhydrous potassium carbonate (0.50 g) in tetrahydrofuran (5 ml) was refluxed under heating for 36 hours. To the reaction solution was added water and the solution was extracted with ethyl acetate. After washing with a saturated aqueous solution of sodium chloride, the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (15 g) and elution with a hexane-ethyl acetate (2:1) mixture gave 0.80 g of ethyl 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylate.

Workup

  1. temperatureunder heating for 36 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. washAfter washing with a saturated aqueous solution of sodium chloride
  4. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resultant residue was subjected to silica gel column chromatography (15 g) and elution with a hexane-ethyl acetate (2:1) mixture

Sources & evidence

ORD record
ord-e2cbc402731c4908aa4adca5f5576059
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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