Tetrahydrofuran → Benzyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

HRID 265902Notes

Reaction equation

HRID 265902 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C[O:37]CC1>CCOC(C)=O>[CH2:23]([O:30][C:31]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:37])[CH2:2][CH2:3]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 92467p-(1-Piperazinyl)phenol

Product 1

HCID 19034142Benzyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-Piperazinyl phenol (Schweizerhall, 5 g, 30.5 mmol) was dissolved in THF (150 mL), treated with diisopropylethylamine (12.2 mL, 70.0 mmol), and cooled to 0° C. Benzylchloroformate (4.4 mL, 30.5 mmol) was added and the reaction was allowed to warm to room temperature and stir overnight. The solution was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated to give a brown oil. Column chromatography (SiO2, 40% EtOAc/hexanes) gave 28-2 as a white solid. Rf (40% EtoAc/hexanes) 0.34.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil

Sources & evidence

ORD record
ord-87ec6e79614e406cac5ae73afa6d6f1a
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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