1-(2-Methoxyphenyl)piperazine → Ethyl 4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoate

HRID 1724642Notes

Reaction equation

HRID 1724642 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.Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[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]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 11370225Ethyl 4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoateYield 68.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 1-(2-methoxyphenyl)piperazine (1.50 g, 7.8 mmol), ethyl 4-bromobutanoate (0.9 mL, 6.3 mmol), and K2CO3 (0.87 g, 6.3 mmol) in acetonitrile was refluxed overnight. After the mixture was cooled, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with CH2Cl2 (230 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/AcOEt, 1:1, as eluent) to afford pure 13 as a pale yellow oil (1.32 g, 68% yield). 1H NMR: δ 1.24 (t, 3H, J=7.1 Hz, CH2CH3), 1.79-1.89 (m, 2H, CH2CH2CO), 2.34 (t, 2H, J=7.3 Hz, COCH2), 2.41 [t, 2H, J=7.4 Hz, (CH2)2NCH2], 2.63 [br s, 4H, (CH2)2NCH2], 3.06 [br s, 4H, ArN(CH2)2], 3.83 (s, 3H, OCH3), 4.11 (q, 2H, J=7.1 Hz, CH2CH3), 6.82-7.00 (m, 3H, aromatic). GC-MS m/z 307 (M++1, 18), 306 (M+, 77), 261 (32), 205 (100), 190 (37).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter the mixture was cooled
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with CH2Cl2 (230 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/AcOEt, 1:1, as eluent)

Sources & evidence

ORD record
ord-e344aa542c6f4b8c9f41587eda4d2d23
Source dataset
uspto-grants-2009_02
Patent number
US07488730B2

Reaction notes

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