Ethyl Acetate → Ethyl 4-(4-oxo-piperidin-1-yl)-phenylcarbamate

HRID 1900077Notes

Reaction equation

HRID 1900077 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(OCC)(=O)C>O1CCCC1.O>[O:14]=[C:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:21](=[O:22])[O:23][CH2:24][CH3:25])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 222202411-(4-Aminophenyl)piperidin-4-one

Product 1

HCID 23371821Ethyl 4-(4-oxo-piperidin-1-yl)-phenylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

4.9 g of 1-(4-aminophenyl)-4-piperidinone were suspended in a mixture of 30 ml of tetrahydrofuran and 9 ml of water under argon and treated with 3.3 g of sodium hydrogen carbonate. Then, a solution of 2.7 ml of ethyl chloroformate in 20 ml of tetrahydrofuran was added dropwise at room temperature while stirring vigorously and, after completion of-the addition, the mixture was stirred for a further 1 h. After adding water and ethyl acetate the phases were separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated. The residue (6.6 g) was chromatographed over silica gel 60 with ethyl acetate/hexane mixtures (1:2-1:0). Crystallization from diethyl ether yielded 3.8 g of ethyl 4-(4-oxo-piperidin-1-yl)-phenylcarbamate as grey crystals. M.p.: 145°-146°.

Workup

  1. additionafter completion of-the addition
  2. stirringthe mixture was stirred for a further 1 h
  3. customwere separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue (6.6 g) was chromatographed over silica gel 60 with ethyl acetate/hexane
  8. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-9916b821197747aa95dabceb8f1918bb
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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