Реакция #2175418

Уравнение реакции

4-(4-hydroxy-phenyl)-1-acetylpiperazine

NaH

phenol

2-bromoethyl methyl ether

→

1-(4-(2-Methoxyethoxy)phenyl)piperazine

Растворители

DMF

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrate
2. 2
   Другоеpartition between EtOAc and 5% citric acid
3. 3
   ПромывкаWash the organic with 1N NaOH
4. 4
   СушкаDry over MgSO4
5. 5
   Концентрированиеconcentrate

Методика

1-(4-(2-Methoxyethoxy)phenyl)piperazine is prepared from 4-(4-hydroxy-phenyl)-1-acetylpiperazine. To NaH (60% in mineral oil, 0.79 g, 20 mmol) in DMF (25 ml) add the phenol (3.0 g, 13.6 mmol), followed by 2-bromoethyl methyl ether (2.27 g, 16.3 mmol). Stir at RT 18 h, concentrate, and partition between EtOAc and 5% citric acid. Wash the organic with 1N NaOH, then brine. Dry over MgSO4, and concentrate to obtain the alkylated product as a white solid. Heat this material (2.2 g, 7.9 mmol) in 6N HCl (30 ml) at reflux for 1 h. Allow to cool and basify to pH=10 with NaOH. Extract with CH2Cl2 and wash with water and then brine. Dry the organic with MgSO4 and concentrate to give the piperazine as a yellow oil.

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