m-Chloroperbenzoic acid → HCID 20294531, compound

HRID 1389995Notes

Reaction equation

HRID 1389995 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[CH3:12][C:13]([CH3:31])([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21](CC2C=CC=CC=2)[CH2:20][CH2:19]1)=[O:17])[CH3:14]>C(Cl)(Cl)Cl>[CH3:14][C:13]([CH3:31])([O:15][C:16]([N:18]1[CH2:19][CH2:20][N:21]([O:10][CH2:8][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)[CH2:22][CH2:23]1)=[O:17])[CH3:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 584330Tert-butyl 4-benzylpiperazine-1-carboxylate

Product 1

HCID 20294531HCID 20294531, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 10.0 g (0.058 mole) m-chloroperbenzoic acid in 100 ml chloroform was added over a one hour period to a cooled (0°-5° C.) solution of 16.1 g (0.058 mole) 1-[1,1-dimethylethoxycarbonyl]-4-phenylmethylpiperazine in 200 ml chloroform. External cooling was removed and the solution stirred for 96 hours at room temperature. The solution was then successively passed through four alumina-packed columns (2.2×16 cm), the eluent evaporated in vacuo, treated with 200 ml acetone and diluted with 50 ml hexane to yield 9.0 g white, crystalline solid, m.p. 123°-126° C. (sealed capillary). An analytical sample from a prior run gave a satisfactory elemental analysis. Calc. for C16H29N2O3.H2O (310.40): C, 61.91; H, 8.44; N, 9.03; O, 20.62. Found: C, 61.91; H, 8.27; N, 9.07; O, 20.55.

Workup

  1. temperatureExternal cooling
  2. customwas removed
  3. customthe eluent evaporated in vacuo
  4. additiontreated with 200 ml acetone
  5. additiondiluted with 50 ml hexane
  6. customto yield 9.0 g white
  7. customcrystalline solid, m.p. 123°-126° C. (sealed capillary)
  8. customAn analytical sample from a prior run gave a satisfactory elemental analysis

Sources & evidence

ORD record
ord-6b88153108324016a091f7126f27f149
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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