1-Benzylpiperazin-2-one hydrochloride → Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

HRID 484968Notes

Reaction equation

HRID 484968 reaction equation
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2=[O:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21](ON=C(C1C=CC=CC=1)C(N)=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1C=CC=CC=1>[C:16]([O:20][C:21]([N:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10](=[O:15])[CH2:11]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 127445191-Benzylpiperazin-2-one hydrochlorideHCID 537190902-(t-Butoxycarbonyloxyimino)-2-phenylacetamide

Product 1

HCID 10891590Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(phenylmethyl)piperazinone (XIV, Example 40, 19.0 g., 0.1 mole) and 2-(t-butoxycarbonyloxyimino)-2-phenylacetamide (30.0 g., 0.12 mole) in benzene (200 ml.) is heated under reflux for 1 hour. The benzene is removed under reduced pressure, the residual oil is dissolved in ethyl acetate:SSB (1:1) and chromatographed on silica gel. The column is eluted with ethyl acetate, the appropriate fractions are pooled, concentrated and the product is crystallized from ethyl acetate:SSB (1:10) to give the title compound, m.p. 89°-90°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. customThe benzene is removed under reduced pressure
  4. dissolutionthe residual oil is dissolved in ethyl acetate
  5. customSSB (1:1) and chromatographed on silica gel
  6. washThe column is eluted with ethyl acetate
  7. concentrationconcentrated
  8. customthe product is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-21d8bf145eaf42c19ca8f0889c9b5263
Source dataset
uspto-grants-1985_08
Patent number
US04534897

Reaction notes

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