Ethyl Acetate → Benzyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate

HRID 2066389Notes

Reaction equation

HRID 2066389 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(OCC)(=O)C>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 27365971-(3-Hydroxyphenyl)piperazine

Product 1

HCID 67387981Benzyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Hydroxyphenyl)piperazine (200 mg) was dissolved in tetrahydrofuran (10 ml), the solution was added with saturated aqueous sodium hydrogencarbonate (10 ml) and benzyl chloroformate (176 μl) at room temperature, and the mixture was stirred for 14 hours. The reaction mixture was added with ethyl acetate for extraction, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (342 mg).

Workup

  1. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-504d3fdfe5564f24a132efaa8e7eb711
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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